Download PDF
Synlett 2011(2): 143-160  
DOI: 10.1055/s-0030-1259297
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of Indole Alkaloids from Chiral Lactams

Mercedes Amat*, Maria Pérez, Joan Bosch
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain
Fax: +34(93)4024539; e-Mail: amat@ub.edu;
Further Information

Publication History

Received 20 October 2010
Publication Date:
04 January 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

This account reports on the use of (R)- or (S)-phenylglycinol- and (S)-tryptophanol-derived oxazolopiperidone lactams as building blocks for the enantioselective synthesis of structurally diverse indole alkaloids.

1 Introduction

2 Monoterpenoid Indole Alkaloids from (R)- or (S)-Phenyl­glycinol-Derived Lactams

2.1 Substituted Piperidines as Precursors for the Enantioselective Synthesis of Indole Alkaloids

2.1.1 (+)-Decarbomethoxytetrahydrosecodine

2.1.2 Enantiopure cis- and trans-(3-Ethylpiperidin-4-yl)acetates as Precursors for the Synthesis of Indolo- and Benzo-[a]quinolizidine Alkaloids

2.1.3 Indole Alkaloids Related to Cleavamine and Quebrach-amine

2.2 Uleine and Strychnos Alkaloids

2.3 The Ervatamine-Silicine Group

3 Indolo[2,3-a]quinolizidines from (S)-Tryptophanol-­Derived Lactams

3.1 Indolo[2,3-a]quinolizidines and Analogues by Intramolecular Amidoalkylation Reactions: Synthesis of (R)-(+)-­Deplancheine and (R)-(+)-Harmicine

3.2 Indolo[2,3-a]quinolizidines by a Modified Bischler-­Napieralski Reaction: Formal Synthesis of (+)-Dihydro­corynantheine and (-)-Dihydrocorynantheol

4 Conclusion

Key words

alkaloids - lactams - indoles - stereoselective synthesis - total synthesis

    References

  • 1a Strunz GM. Findlay JA. In The Alkaloids   Vol. 26:  Brossi A. Academic; London: 1985.  p.89-183  
    Google Scholar
  • 1b Takahata H. Momose T. In The Alkaloids   Vol. 44:  Cordell GA. Academic; San Diego: 1993.  p.189-256  
    Google Scholar
  • 1c Ohmiya S. Saito K. Murakoshi I. In The Alkaloids   Vol. 47:  Cordell GA. Academic; San Diego: 1995.  p. 1-114  
    Google Scholar
  • 1d Schneider MJ. In Alkaloids: Chemical and Biological Perspectives   Vol. 10:  Pelletier SW. Pergamon; Oxford: 1996.  p.155-299  
    Google Scholar
  • 1e Andersen RJ. Van Soest RWM. Kong F. In Alkaloids: Chemical and Biological Perspectives   Vol. 10:  Pelletier SW. Pergamon; Oxford: 1996.  p.301-355  
    Google Scholar
  • 1f Daly JW. Garraffo HM. Spande TF. In Alkaloids: Chemical and Biological Perspectives   Vol. 13:  Pelletier SW. Pergamon; New York: 1999.  p.1-161  
    Google Scholar
  • 1g Watson PS. Jiang B. Scott B. Org. Lett.  2000,  2:  3679-3681  
    Google Scholar
  • 1h Michael JP. Nat. Prod. Rep.  2005,  22:  603-626  
    Google Scholar
  • 2a Angle SR. Breitenbucher JG. In Studies in Natural Products Chemistry   Vol. 16:  . Elsevier; Amsterdam: 1995.  p.453-502  
    Google Scholar
  • 2b Laschat S. Dickner T. Synthesis  2000,  1781 
    Google Scholar
  • 2c Guilloteau-Bertin B. Compère D. Gil L. Marazano C. Das BC. Eur. J. Org. Chem.  2000,  1391 
    Google Scholar
  • 2d Weintraub PM. Sabol JS. Kane JM. Borcherding DR. Tetrahedron  2003,  59:  2953 
    Google Scholar
  • 2e Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
    Google Scholar
  • 2f Buffat MGP. Tetrahedron  2004,  60:  1701 
    Google Scholar
  • 2g Pearson MSM. Mathe-Allainmat M. Fargeas V. Lebreton J. Eur. J. Org. Chem.  2005,  2159 
    Google Scholar
  • 2h Fraser HL. Floyd MB. Sosa ACB. Prog. Heterocycl. Chem.  2005,  17:  261 
    Google Scholar
  • 2i Huang P.-Q. Synlett  2006,  1133 
    Google Scholar
  • 2j De Risis C. Fanton G. Pollini GP. Trapella C. Valente F. Zanirato V. Tetrahedron: Asymmetry  2008,  19:  131 
    Google Scholar
  • 2k Kaellstroem S. Leino R. Bioorg. Med. Chem.  2008,  16:  601 
    Google Scholar
  • 2l Vicario JL. Badía D. Carrillo L. Ruiz N. Reyes E. In Targets in Heterocyclic Systems: Chemistry and Properties   Vol. 12:  Attanasi OA. Spinelli D. Italian Society of Chemistry; Rome: 2008.  p.302-327  
    Google Scholar
  • 3a Romo D. Meyers AI. Tetrahedron  1991,  47:  9503 
    Google Scholar
  • See also:
  • 3b Stereocontrolled Organic Synthesis   Trost BM. Blackwell; Oxford: 1994. 
    Google Scholar
  • 4 Meyers AI. Brengel GP. Chem. Commun. (Cambridge)  1997,  1 
    Google Scholar
  • 5 Groaning MD. Meyers AI. Tetrahedron  2000,  56:  9843 
    CrossrefGoogle Scholar
  • 6a Amat M. Llor N. Hidalgo J. Bosch J. Molins E. Miravitlles C. Tetrahedron: Asymmetry  1996,  7:  2501 
    Google Scholar
  • 6b Amat M. Llor N. Bosch J. Solans X. Tetrahedron  1997,  53:  719 
    Google Scholar
  • 6c Amat M. Bosch J. Hidalgo J. Cantó M. Pérez M. Llor N. Molins E. Miravitlles C. Orozco M. Luque J. J. Org. Chem.  2000,  65:  3074 
    Google Scholar
  • 6d Amat M. Llor N. Huguet M. Molins E. Espinosa E. Bosch J. Org. Lett.  2001,  3:  3257 
    Google Scholar
  • 6e Amat M. Cantó M. Llor N. Bosch J. Chem. Commun. (Cambridge)  2002,  526 
    Google Scholar
  • 6f Amat M. Llor N. Escolano C. Huguet M. Pérez M. Molins E. Bosch J. Tetrahedron: Asymmetry  2003,  14:  293 
    Google Scholar
  • 6g Amat M. Llor N. Hidalgo J. Escolano C. Bosch J. J. Org. Chem.  2003,  68:  1919 
    Google Scholar
  • 6h Amat M. Escolano C. Llor N. Huguet M. Pérez M. Bosch J. Tetrahedron: Asymmetry  2003,  14:  1679 
    Google Scholar
  • 6i Casamitjana N. Amat M. Llor N. Carreras M. Pujol X. Fernández MM. López V. Molins E. Miravitlles C. Bosch J. Tetrahedron: Asymmetry  2003,  14:  2033 
    Google Scholar
  • 6j Amat M. Huguet M. Llor N. Bassas O. Gomez AM. Bosch J. Badia J. Baldoma L. Aguilar J. Tetrahedron Lett.  2004,  45:  5355 
    Google Scholar
  • 7a Amat M. Cantó M. Llor N. Ponzo V. Pérez M. Bosch J. Angew. Chem. Int. Ed.  2002,  41:  335 
    Google Scholar
  • 7b Amat M. Cantó M. Llor N. Escolano C. Molins E. Espinosa E. Bosch J. J. Org. Chem.  2002,  67:  5343 
    Google Scholar
  • 7c Amat M. Bassas O. Pericàs MA. Pastó M. Bosch J. Chem. Commun. (Cambridge)  2005,  1327 
    Google Scholar
  • 7d Amat M. Bassas O. Llor N. Cantó M. Pérez M. Molins E. Bosch J. Chem. Eur. J.  2006,  12:  7872 
    Google Scholar
  • See also:
  • 7e Amat M. Pérez M. Llor N. Bosch J. Lago E. Molins E. Org. Lett.  2001,  3:  611 
    Google Scholar
  • 7f Amat M. Pérez M. Llor N. Bosch J. Org. Lett.  2002,  4:  2787 
    Google Scholar
  • 7g Amat M. Pérez M. Minaglia AT. Casamitjana N. Bosch J. Org. Lett.  2005,  7:  3653 
    Google Scholar
  • 7h Soteras I. Lozano O. Gómez-Esqué A. Escolano C. Orozco M. Amat M. Bosch J. Luque FJ. J. Am. Chem. Soc.  2006,  128:  6581 
    Google Scholar
  • 7i Amat M. Escolano C. Gómez-Esqué A. Lozano O. Llor N. Griera R. Molins E. Bosch J. Tetrahedron: Asymmetry  2006,  17:  1581 
    Google Scholar
  • 7j Allin SM. Duffy LJ. Bulman Page PC. McKee V. Edgar M. McKenzie MJ. Amat M. Bassas O. Santos MMM. Bosch J. Tetrahedron Lett.  2006,  47:  5713 
    Google Scholar
  • 7k Amat M. Pérez M. Minaglia AT. Peretto B. Bosch J. Tetrahedron  2007,  63:  5839 
    Google Scholar
  • 7l Amat M. Pérez M. Minaglia AT. Bosch J. J. Org. Chem.  2008,  73:  6920 
    Google Scholar
  • 7m Amat M. Pérez M. Minaglia AT. Passarella D. Bosch J. Tetrahedron: Asymmetry  2008,  19:  2406 
    Google Scholar
  • 7n Amat M. Brunaccini E. Checa B. Pérez M. Llor N. Bosch J. Org. Lett.  2009,  11:  4370 
    Google Scholar
  • 7o Amat M. Pérez M. Proto S. Gatti T. Bosch J. Chem. Eur. J.  2010,  16:  9438 
    Google Scholar
  • 8a Amat M. Griera R. Fabregat R. Molins E. Bosch J. Angew. Chem. Int. Ed.  2008,  47:  3348 
    Google Scholar
  • 8b Amat M. Fabregat R. Griera R. Bosch J. J. Org. Chem.  2009,  74:  1794 
    Google Scholar
  • 8c Amat M. Fabregat R. Griera R. Florindo P. Molins E. Bosch J. J. Org. Chem.  2010,  75:  3797 
    Google Scholar
  • 9 Escolano C. Amat M. Bosch J. Chem. Eur. J.  2006,  12:  8198 
    CrossrefGoogle Scholar
  • 10 Gaskell SN. Duffy LJ. Allin SM. Nat. Prod. Commun.  2008,  3:  1825 
    Google Scholar
  • 11a Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds   Vol. 25, Part 4:  Saxton JE. Weissberger A. Taylor EC. Wiley; New York: 1983. 
    Google Scholar
  • 11b Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds   Suppl. to Vol. 25, Part 4:  Saxton JE. Taylor EC. Wiley; Chichester: 1994. 
    Google Scholar
  • See also:
  • 11c Leonard J. Nat. Prod. Rep.  1999,  16:  319 
    Google Scholar
  • 11d Borschberg H.-J. Curr. Org. Chem.  2005,  9:  1465 
    Google Scholar
  • 11e Edwankar CR. Edwankar RV. Namjoshi OA. Rallapalli SK. Yang J. Cook JM. Curr. Opin. Drug Discovery Dev.  2009,  12:  752 
    Google Scholar
  • 12a O’Connor SE. Maresh JJ. Nat. Prod. Rep.  2006,  23:  532 
    Google Scholar
  • 12b Stöckigt J. Barleben L. Panjikar S. Loris EA. Plant Physiol. Biochem.  2008,  46:  340 
    Google Scholar
  • 13a Danieli B. Palmisano G. In The Alkaloids   Vol. 27:  Brossi A. Academic; Orlando: 1986.  p.1-130  
    Google Scholar
  • 13b Scott AI. Acc. Chem. Res.  1970,  3:  151 
    Google Scholar
  • 14 Amat M. Llor N. Hidalgo J. Bosch J. Tetrahedron: Asymmetry  1997,  8:  2237 
    CrossrefGoogle Scholar
  • 15 Amat M. Escolano C. Llor N. Lozano O. Gómez-Esqué A. Griera R. Bosch J. ARKIVOC  2005,  (ix):  115 
    Google Scholar
  • 16a Amat M. Pshenichnyi G. Bosch J. Molins E. Miravitlles C. Tetrahedron: Asymmetry  1996,  7:  3091 
    Google Scholar
  • 16b

    See also ref. 15

  • 17a Crooks PA. Robinson B. Smith GF. Chem. Commun.  1968,  1210 
    Google Scholar
  • For further isolations from other species, see:
  • 17b Robert GMT. Ahond A. Poupat C. Potier P. Jollés C. Jousselin A. Jacquemin H. J. Nat. Prod.  1983,  46:  694 
    Google Scholar
  • 17c . Zaman K. Perveen S. . Muzaffar A. Choudhary MI. Pervin A. Phytochemistry  1991,  30:  1285 
    Google Scholar
  • 17d Mroue MA. Ghuman MA. Alam M. Phytochemistry  1993,  33:  217 
    Google Scholar
  • 18 Palmisano G. Santagostino M. Riva S. Sisti M. Tetrahedron: Asymmetry  1995,  6:  1229 
    CrossrefGoogle Scholar
  • 19 Amat M. Hadida S. Sathyanarayana S. Bosch J. J. Org. Chem.  1994,  59:  10 
    CrossrefGoogle Scholar
  • 20a Battersby AR. Parry RJ. J. Chem. Soc. D  1971,  901 
    Google Scholar
  • 20b Jain S. Sinha A. Bhakuni DS. Phytochemistry  2002,  60:  853 
    Google Scholar
  • 21a Uskokovic M. Reese C. Lee HL. Grethe G. Gutzwiller J. J. Am. Chem. Soc.  1971,  93:  5902 
    Google Scholar
  • 21b Uskokovic MR. Henderson T. Reese C. Lee HL. Grethe G. Gutzwiller J. J. Am. Chem. Soc.  1978,  100:  571 
    Google Scholar
  • 21c Fujii T. Ohba M. Yoneyama K. Kizu H. Chem. Pharm. Bull.  1985,  33:  358 
    Google Scholar
  • 21d Minato D. Imai M. Kanda Y. Onomura O. Matsumura Y. Tetrahedron Lett.  2006,  47:  5485 
    Google Scholar
  • 22a Fujii T. Yoshifuji S. Tai M. Chem. Pharm. Bull.  1975,  23:  2094 
    Google Scholar
  • 22b Fujii T. Ohba M. Chem. Pharm. Bull.  1985,  33:  583 
    Google Scholar
  • 22c Brown RT. Leonard J. Tetrahedron Lett.  1978,  19:  1605 
    Google Scholar
  • 23a Hirai Y. Terada T. Yamazaki T. Momose T. J. Chem. Soc., Perkin Trans. 1  1992,  517 
    Google Scholar
  • See also:
  • 23b Hirai Y. Terada T. Yamazaki T. Momose T.
    J. Chem. Soc., Perkin Trans. 1  1992,  509 
    Google Scholar
  • 24 Amat M. Pérez M. Llor N. Escolano C. Luque FJ. Molins E. Bosch J. J. Org. Chem.  2004,  69:  8681 
    CrossrefGoogle Scholar
  • 25 Deslongchamps P. In Stereoelectronic Effects in Organic Chemistry   Pergamon; Oxford: 1983.  p.221 
    Google Scholar
  • 26 Perlmutter P. In Conjugate Addition Reactions in Organic Synthesis   Pergamon; Oxford: 1992.  p.25 
    Google Scholar
  • 27a Fujii T. Ohba M. Yoneyama K. Kizu H. Yoshifuji S. Chem. Pharm. Bull.  1986,  34:  669 
    Google Scholar
  • 27b Fujii T. Ohba M. Heterocycles  1998,  47:  525 ; and references cited therein
    Google Scholar
  • 28a Edwin SJ. In The Alkaloids   Vol. 50:  Cordell GA. Academic; San Diego: 1998.  p.343-376  
    Google Scholar
  • 28b Overman LE. Sworin M. In Alkaloids: Chemical and Biological Perspectives   Vol. 3:  Pelletier SW. John Wiley and Sons; New York: 1985.  p.275-307  
    Google Scholar
  • 28c Cordell GA. In The Alkaloids   Vol. 17:  Manske RHF. Rodrigo RGA. Academic; New York: 1979.  p.199-384  
    Google Scholar
  • 29a Sundberg RJ. Smith SQ. In The Alkaloids   Vol. 59:  Cordell GA. Elsevier; San Diego: 2002.  p.281-386  
    Google Scholar
  • 29b Takayama H. Sakai S.-I. In The Alkaloids   Vol. 50:  Cordell GA. Elsevier; San Diego: 1998.  p.415-452  
    Google Scholar
  • 30 Amat M. Lozano O. Escolano C. Molins E. Bosch J. J. Org. Chem.  2007,  72:  4431 
    CrossrefGoogle Scholar
  • 31a Ziegler FE. Kloek JA. Zoretic PA. J. Am. Chem. Soc.  1969,  91:  2342 
    Google Scholar
  • See also:
  • 31b Ziegler FE. Bennett GB. J. Am. Chem. Soc.  1973,  95:  7458 
    Google Scholar
  • 32 Takano S. Sato M. Hatakema S. Hirama M. Ogasawara K. Heterocycles  1976,  5:  221 
    CrossrefGoogle Scholar
  • 33a Takano S. Yonaga M. Ogasawara K. J. Chem. Soc., Chem. Commun.  1981,  1153 
    Google Scholar
  • 33b Node M. Nagasawa H. Fuji K. J. Org. Chem.  1990,  55:  517 
    Google Scholar
  • 33c Kozmin SA. Iwama T. Huang Y. Rawal VH. J. Am. Chem. Soc.  2002,  124:  4628 
    Google Scholar
  • 33d Sattely ES. Meek SJ. Malcolmson SJ. Schrock RR. Hoveyda AH. J. Am. Chem. Soc.  2009,  131:  943 
    Google Scholar
  • 34 Amat M. Escolano C. Lozano O. Gómez-Esqué A. Griera R. Molins E. Bosch J. J. Org. Chem.  2006,  71:  3804 
    CrossrefGoogle Scholar
  • 35 For a preliminary account of this work, see: Amat M. Escolano C. Lozano O. Llor N. Bosch J. Org. Lett.  2003,  5:  3139 
    CrossrefGoogle Scholar
  • 36 Danieli B. Lesma G. Passarella D. Silvani A. Tetrahedron Lett.  2000,  41:  3489 
    CrossrefGoogle Scholar
  • 37 Kanada RM. Ogasawara K. Tetrahedron Lett.  2001,  42:  7311 
    CrossrefGoogle Scholar
  • 38a Joule JA. Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds   Vol. 25, Part 4:  Saxton JE. Weissberger A. Taylor EC. Wiley; New York: 1983.  Chap. 6.
    Google Scholar
  • 38b Alvarez M. Joule JA. Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds   Suppl. to Vol. 25, Part 4:  Saxton JE. Taylor EC. Wiley; Chichester: 1994.  Chap. 6.
    Google Scholar
  • 38c Alvarez M. Joule JA. In The Alkaloids   Vol. 57:  Cordell GA. Academic; New York: 2001.  Chap. 4.
    Google Scholar
  • 39 Amat M. Llor N. Checa B. Pérez M. Bosch J. Tetrahedron Lett.  2007,  48:  6722 
    CrossrefGoogle Scholar
  • 40 For a preliminary account of this work, see: Amat M. Pérez M. Llor N. Martinelli M. Molins E. Bosch J. Chem. Commun. (Cambridge)  2004,  1602 
    Google Scholar
  • 41 Saito M. Kawamura M. Hiroya K. Ogasawara K. Chem. Commun. (Cambridge)  1997,  765 
    Google Scholar
  • 42a Joule JA. Ohashi M. Gilbert B. Djerasi C. Tetrahedron  1965,  21:  1717 
    Google Scholar
  • 42b Gràcia J. Casamitjana N. Bonjoch J. Bosch J. J. Org. Chem.  1994,  59:  3939 
    Google Scholar
  • 43 Ishikura M. Takahashi N. Yamada K. Abe T. Heterocycles  2008,  75:  107 
    CrossrefGoogle Scholar
  • 44 Wu A. Snieckus V. Tetrahedron Lett.  1975,  16:  2057 
    CrossrefGoogle Scholar
  • 45 Amat M. Coll M.-D. Bosch J. Espinosa E. Molins E. Tetrahedron: Asymmetry  1997,  8:  935 
    CrossrefGoogle Scholar
  • 46a Joule JA. Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds   Vol. 25, Part 4:  Saxton JE. Weissberger A. Taylor EC. Wiley; New York: 1983.  p.232 
    Google Scholar
  • 46b

    See also ref. 13a. For more-recent isolations, see:

  • 46c Zhang H. Yue J.-M. Helv. Chim. Acta  2005,  88:  2537 
    Google Scholar
  • 47 Amat M. Llor N. Checa B. Molins E. Bosch J. J. Org. Chem.  2010,  75:  178 
    CrossrefGoogle Scholar
  • For related synthetic studies on the ervatamine-silicine group, see:
  • 48a Husson H.-P. Bannai K. Freire R. Mompon B. Reis FAM. Tetrahedron  1978,  34:  1363 
    Google Scholar
  • 48b Bennasar M.-L. Vidal B. Bosch J. J. Org. Chem.  1997,  62:  3597 
    Google Scholar
  • 48c Bennasar M.-L. Vidal B. Kumar R. Lázaro A. Bosch J. Eur. J. Org. Chem.  2000,  3919 
    Google Scholar
  • For the synthesis of tetracyclic structures related to ervatamine-silicine alkaloids, see:
  • 48d Langlois Y. Potier P. Tetrahedron  1975,  31:  423 
    Google Scholar
  • 48e Grierson DS. Bettiol J.-L. Buck I. Husson H.-P. Rubiralta M. Diez A. J. Org. Chem.  1992,  57:  6414 
    Google Scholar
  • 49 For a preliminary account of this work, see: Amat M. Checa B. Llor N. Molins E. Bosch J. Chem. Commun. (Cambridge)  2009,  2935 
    Google Scholar
  • 51a Bassas O. Llor N. Santos MMM. Griera R. Molins E. Amat M. Bosch J. Org. Lett.  2005,  7:  2817 
    Google Scholar
  • 51b Amat M. Santos MMM. Bassas O. Llor N. Escolano C. Gómez-Esqué A. Molins E. Allin SM. McKee V. Bosch J. J. Org. Chem.  2007,  72:  5193 
    Google Scholar
  • See also:
  • 51c Santos MMM. In Heterocyclic Targets in Advanced Organic Synthesis   Carreiras MC. Marco-Contelles J. Research Signpost; Trivandrum / India: 2001.  p.69-82  
    Google Scholar
  • 52 Allin SM. Thomas CI. Allard JE. Duncton M. Elsegood MRJ. Edgar M. Tetrahedron Lett.  2003,  44:  2335 
    CrossrefGoogle Scholar
  • 53a Allin SM. Thomas CI. Allard JE. Doyle K. Elsegood MRJ. Tetrahedron Lett.  2004,  45:  7103 
    Google Scholar
  • 53b Allin SM. Thomas CI. Allard JE. Doyle K. Elsegood MRJ. Eur. J. Org. Chem.  2005,  4179 
    Google Scholar
  • 54 Allin SM. Northfield CJ. Page MI. Slawin AMZ. Tetrahedron Lett.  1998,  39:  4905 
    CrossrefGoogle Scholar
  • 55 Allin SM. Gaskell SN. Elsegood MRJ. Martin WP. Tetrahedron Lett.  2007,  48:  5669 
    CrossrefGoogle Scholar
  • 56 Allin SM. Thomas CI. Doyle K. Elsegood MRJ.
    J. Org. Chem.  2005,  70:  357 
    CrossrefGoogle Scholar
  • 57 Amat M. G ómez-Esqué A. Escolano C. Santos MMM. Molins E. Bosch J. J. Org. Chem.  2009,  74:  1205 
    CrossrefGoogle Scholar
  • 58 Tietze LF. Zhou Y. Angew. Chem. Int. Ed.  1999,  38:  2045 
    CrossrefGoogle Scholar
  • 59a Weisbach JA. Kirkpatrick JL. Williams KR. Anderson EL. Yim NC. Douglas B. Tetrahedron Lett.  1965,  6:  3457 
    Google Scholar
  • 59b Van Tamelen EE. Hester JB.
    J. Am. Chem. Soc.  1969,  91:  7342 
    Google Scholar
  • 60a Brown RT. Jones MF. Wingfield M. J. Chem. Soc., Chem. Commun.  1984,  847 
    Google Scholar
  • 60b Diez A. Vila C. Sinibaldi ME. Troin Y. Rubiralta M. Tetrahedron Lett.  1993,  34:  733 
    Google Scholar
  • For previous syntheses of (-)-dihydrocorynantheol, see:
  • 61a Suzuki T. Sato E. Unno K. Kametani T. Chem. Pharm. Bull.  1986,  34:  1584 
    Google Scholar
  • 61b Beard RL. Meyers AI. J. Org. Chem.  1991,  56:  2091 
    Google Scholar
  • 61c Ohba M. Ohashi T. Fujii T. Heterocycles  1991,  32:  319 
    Google Scholar
  • 61d Itoh T. Tokoya M. Miyauchi K. Nagata K. Ohsawa A. Org. Lett.  2006,  8:  1533 
    Google Scholar
  • 61e Tosaka A. Ito S. Miyazawa N. Shibuya M. Ogasawara K. Iwabuchi Y. Heterocycles  2006,  70:  153 
    Google Scholar
  • 62 Deiters A. Pettersson M. Martin SF. J. Org. Chem.  2006,  71:  6547 
    Google Scholar
  • 63 For the conversion of (-)-dihydrocorynantheine into (-)-rhynchophylline and (+)-isorhynchophylline, see: Finch N. Taylor WI. J. Am. Chem. Soc.  1962,  84:  3871 
    CrossrefGoogle Scholar
50

For a review of the work developed by S. M. Allin in this field, see: ref. 10