Total Syntheses of Natural Products Featuring Intramolecular O-Alkylations Involving Positions β to a Carbonyl Group as the Key Step

Dedicated to my mentor Professor Per Ahlberg on the occasion of his 75^th birthday

Abstract

Surveyed in this account are the syntheses of nocardiolactone, valilactone, nonactin, pamamycin 621A, and IKD-8344 performed by our group. The key step of these formations is intramolecular O-alkylation involving positions extremely liable to β-elimination under conventional alkylation conditions.

1 Introduction

2 Nocardiolactone

3 Valilactone

4 Nonactin

5 Pamamycin 621A

6 IKD-8344

7 Summary

Key words

antibiotics - O-alkylation - aldol reaction - cyclization - lactones

• References


For general references, see:
• 1a Williamson W. Justus Liebigs Ann. Chem. 1851; 77: 37
• 1b Koert U. Synthesis 1995; 115
• 2 Mikami Y, Yazawa Y, Tanaka Y, Ritzau M, Grafe U. Nat. Prod. Lett. 1999; 13: 277
• 3 Kitahara M, Asano M, Naganawa H, Maeda K, Hamada M, Aoyagi T, Umezawa H, Iitaka Y, Nakamura H. J. Antibiot. 1987; 40: 1647

For reviews, see:
• 4a Keller-Schierlein W, Gerlach H. Fortschr. Chem. Org. Naturst. 1968; 26: 161
• 4b Nawata Y, Ando K, Iitaka Y. Met. Ions Biol. Syst. 1985; 19: 207
• 4c Zizka Z. Folia Microbiol. 1998; 43: 7
• 5a McCann PA, Pogell BM. J. Antibiot. 1979; 32: 673
• 5b Kondo S, Yasui K, Natsume M, Katayama M, Marumo S. J. Antibiot. 1988; 41: 1196
• 5c Natsume M, Kondo S, Marumo S. J. Chem. Soc., Chem. Commun. 1989; 1911
• 5d Natsume M, Yasui K, Kondo S, Marumo S. Tetrahedron Lett. 1991; 32: 3087
• 5e Natsume M, Tazawa J, Yagi K, Abe H, Kondo S, Marumo S. J. Antibiot. 1995; 48: 1159
• 5f Natsume M, Honda A, Oshima Y, Abe H, Kondo S, Tanaka F, Marumo S. Biosci. Biotechnol., Biochem. 1995; 59: 1766

For a review, see:
• 5g Metz P. Top. Curr. Chem. 2005; 244: 215
• 6a Minami Y, Yoshida K, Azuma R, Nishii M, Inagaki J, Nohara F. Tetrahedron Lett. 1992; 33: 7373
• 6b Ishida T, In Y, Nishii M, Minami Y. Chem. Lett. 1994; 1321
• 7a Zhang Y, Gross RA, Lenz RW. Macromolecules 1990; 23: 3206
• 7b De Angelis F, De Fusco E, Desiderio P, Giannessi F, Piccirilli F, Tinti MO. Eur. J. Org. Chem. 1999; 2705
• 7c Bernabei I, Castagnani R, De Angelis F, De Fusco E, Giannessi F, Misiti D, Muck S, Scafetta N, Tinti MO. Chem. Eur. J. 1996; 2: 826
• 7d Sato T, Kawara T, Nishizawa A, Fujisawa T. Tetrahedron Lett. 1980; 21: 3377
• 8a Sun Y.-P, Wu Y.-K. Synlett 2005; 1477

Erratum, see:
• 8b Sun Y.-P, Wu Y.-K. Synlett 2006; 1322

For another synthesis, see:
• 8c Kumaraswamy G, Markondaiah B. Tetrahedron 2008; 64: 5861
• 9a Evans DA, Bartroli J, Shih TL. J. Am. Chem. Soc. 1981; 103: 2127
• 9b Evans DA, Rieger DL, Bilodeau MT, Urpi F. J. Am. Chem. Soc. 1991; 113: 1047
• 10a Crimmins MT, King BW, Tabet EA. J. Am. Chem. Soc. 1997; 119: 7883
• 10b Crimmins MT, Chaudhary K. Org. Lett. 2000; 2: 775
• 10c Crimmins MT, King BW, Tabet EA, Chaudhary K. J. Org. Chem. 2001; 66: 894
• 11 Wu Y.-K, Sun Y.-P, Yang Y.-Q, Hu Q, Zhang Q. J. Org. Chem. 2004; 69: 6141
• 12 For a dianion-based approach to selective hydroxyl group activation and subsequent formation of a b-lactone via intramolecular O-alkylation, see: Wu Y.-K, Sun Y.-P. Chem. Commun. (Cambridge) 2005; 1906
• 13a Weibel EK, Hadvary P, Hochuli E, Kupfer E, Lengsfeld H. J. Antibiot. 1987; 40: 1081
• 13b Hochuli E, Kupfer E, Maurer R, Mwister W, Mercadal Y, Schmidt K. J. Antibiot. 1987; 40: 1086
• 13c Bodkin JA, Humphries EJ, McLeod MD. Tetrahedron Lett. 2003; 44: 2869
• 13d Ghosh AK, Fidanze S. Org. Lett. 2000; 2: 2405
• 13e Parson PJ, Cowell JK. Synlett 2000; 107
• 13f Dirat O, Kouklovsky C, Langlois Y. Org. Lett. 1999; 1: 753
• 13g Ghosh AK, Liu C. Chem. Commun. (Cambridge) 1999; 1743
• 13h Paterson I, Doughty VA. Tetrahedron Lett. 1999; 40: 393

For synthetic studies of tetrahydrolipstatin (compound 14), see for example:
• 13i Giese B, Roth M. J. Braz. Chem. Soc. 1996; 7: 243
• 13j Hanessian S, Tehim A, Chen P. J. Org. Chem. 1993; 58: 7768
• 13k Fleming I, Lawrence NJ. J. Chem. Soc., Perkin Trans. 1 1998; 2670
• 13l Pons J.-M, Pommier A, Lerpiniere J, Kocienski P. J. Chem. Soc., Perkin Trans. 1 1993; 1549
• 13m Chadha NK, Tang PC, Courtney LF, Cook CM, Wovkulich PM, Uskokovic MR. J. Org. Chem. 1991; 56: 4714
• 13n Fleming I, Lawrence NJ. Tetrahedron Lett. 1990; 31: 3645
• 13o Barbier P, Schneider F. J. Org. Chem. 1988; 53: 1218
• 13p Barbier P, Schneider F, Widmer U. Helv. Chim. Acta 1987; 70: 1412
• 13q Case-Green SC, Davies SG, Hedgecock CJ. R. Synlett 1991; 781
• 14 Kondo S, Uotani K, Miyamoto M, Hazato T, Naganawa H, Aoyagi T, Umezawa H. J. Antibiot. 1978; 31: 797
• 15a Mutoh M, Nakada N, Matsukuma S, Ohshima S, Yoshinari K, Watanabe J, Arisawa M. J. Antibiot. 1994; 47: 1369
• 15b Yoshinari K, Aoki M, Ohtsuka T, Nakayama N, Itezono Y, Mutoh M, Watanabe J, Yo kose K. J. Antibiot. 1994; 47: 1376

For the synthesis of panclicin D, see:
• 15c Yang H.-W, Zhao C, Romo D. Tetrahedron 1997; 53: 16471

For a simplified analogue, see:
• 15d Cardani S, De Toma C, Gennari C, Scolastico C. Tetrahedron 1992; 48: 5557
• 15e Thadani AN, Batey RA. Tetrahedron Lett. 2003; 44: 8051
• 15f Pommier A, Pons J.-M. Synthesis 1991; 1294
• 15g Polkowska J, Lukaszewicz E, Kiegiel J, Jurczak J. Tetrahedron Lett. 2004; 45: 3873
• 16a Umezawa H, Aoyagi T, Uotani K, Hamada M, Takeuchi T, Takahashi S. J. Antibiot. 1980; 33: 1594
• 16b Uotani K, Naganawa H, Kondo S, Aoyagi T, Umezawa H. J. Antibiot. 1982; 35: 1495

For synthetic examples, see:
• 16c Paterson I, Hulme AN. J. Org. Chem. 1995; 60: 3288
• 16d Mandal AK. Org. Lett. 2002; 4: 2043

For its isolation, see:
• 17a Liu D.-Z, Wang F, Liao T.-G, Tang J.-G, Steglich W, Zhu H.-J, Liu J.-K. Org. Lett. 2006; 8: 5749

For its synthesis, see:
• 17b Zhou Q, Snider BB. Org. Lett. 2008; 10: 1401
• 18a Bate RW, Fernandez-Moro R, Ley SV. Tetrahedron Lett. 1991; 32: 2651
• 18b Bate RW, Fernandez-Moro R, Ley SV. Tetrahedron 1991; 47: 9929

For syntheses from other groups, see:
• 18c Ma G, Zancanella M, Oyola Y, Richardson RD, Smith JW, Romo D. Org. Lett. 2006; 8: 4497
• 18d Case-Green SC, Davies SG, Roberts PM, Russell AJ, Thomson JE. Tetrahedron: Asymmetry 2008; 19: 2620
• 19 Wu Y.-K, Sun Y.-P. J. Org. Chem. 2006; 71: 5748
• 20 For practical access to the oxazolidinethione auxiliaries, see: Wu Y.-K, Yang Y.-Q, Hu Q. J. Org. Chem. 2004; 69: 3990
• 21 Nicolaou KC, Bunnage ME, McGarry DG, Shi S, Somers PK, Wallace PA, Chu X.-J, Agrios KA, Gunzner JL, Yang Z. Chem. Eur. J. 1999; 5: 599
• 22 Evans DA, Chapman KT, Carreira EM. J. Am. Chem. Soc. 1988; 110: 3560
• 23 Mulzer J, Bruntrup G, Chucholowski A. Angew. Chem. Int. Ed. Engl. 1979; 18: 622
• 24 Nefelova MV, Sverdlova AN. Antibiot. Med. Biotekhnol. 1985; 30: 261 ; Chem. Abstr. 1985, 102, 201065
• 25 Oishi H, Sugawa T, Okutomi T, Suzuki K, Hayashi T, Sawada M, Ando K. J. Antibiot. 1970; 23: 105
• 26 Shopotova LP, Shenin YD. Zh. Prikl. Khim. 1993; 66: 1334 ; Chem. Abstr. 1994, 120, 158329
• 27 Borrel MN, Pereira E, Fiallo M, Garnier-Suillerot A. Eur. J. Biochem. 1994; 223: 125
• 28a Callewaert DM, Radcliff G, Tanouchi Y, Shichi H. Immunopharmacol. 1988; 16: 25
• 28b Tanouchi Y, Shichi H. Immunology 1988; 63: 471

There are five total syntheses of nonactin in the literature, see:
• 29a Gerlach H, Oertle K, Thalmann A, Servi S. Helv. Chim. Acta 1975; 58: 2036
• 29b Schmidt U, Gombos J, Haslinger E, Zak H. Chem. Ber. 1976; 109: 2628
• 29c Bartlett PA, Meadows JD, Ottow E. J. Am. Chem. Soc. 1984; 106: 5304
• 29d Kim BH, Lee JY. Tetrahedron 1996; 52: 571
• 29e Fleming I, Ghosh SK. J. Chem. Soc., Perkin Trans. 1 1998; 2733

For a comprehensive review, see:
• 29f Fleming I, Ghosh SK. Stud. Nat. Prod. Chem. 1996; 18: 229

For an analogue, see:
• 29g Coutable L, Adil K, Saluzzo C. Tetrahedron 2008; 64: 11296

For recent syntheses of nonactic acids, see:
• 29h Takai K, Hanadate T, Oi S, Yamada T, Kuwahara S, Kiyota H. Synthesis 2011; 3741
• 29i Loiseau F, Simone J.-M, Carcache D, Bobal P, Neier R. Monatsh. Chem. 2007; 138: 121
• 29j Zhou Y, Xu Q, Zhai H. Tetrahedron Lett. 2008; 49: 5271
• 30 Kusche BR, Smith AE, McGuirl MA, Priestley ND. J. Am. Chem. Soc. 2009; 131: 17155
• 31 Wu Y.-K, Sun Y.-P. Org. Lett. 2006; 8: 2831
• 32 Schaus SE, Brandes BD, Larrow JF, Tokunaga M, Hansen KB, Gould AE, Furrow ME, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 1307
• 33 Řezanka T, Spížek J, Přikrylová V, Prell A, Dembitsky VM. Tetrahedron 2004; 60: 4781

For total syntheses, see:
• 34a Germay O, Kumar N, Thomas EJ. Tetrahedron Lett. 2001; 42: 4969
• 34b Lee E, Jeong EJ, Kang EJ, Sung LT, Hong SK. J. Am. Chem. Soc. 2001; 123: 10131
• 34c Jeong EJ, Kang EJ, Sung LT, Hong SK, Lee E. J. Am. Chem. Soc. 2002; 124: 14655
• 34d Wang Y, Bernsmann H, Gruner M, Metz P. Tetrahedron Lett. 2001; 42: 7801
• 34e Kang SH, Jeong JW, Hwang YS, Lee SB. Angew. Chem. Int. Ed. 2002; 41: 1392
• 34f Lanners S, Norouzi-Arasi H, Salom-Roig XJ, Hanquet G. Angew. Chem. Int. Ed. 2007; 46: 7086
• 34g Fischer P, Segovia AB. G, Gruner M, Metz P. Angew. Chem. Int. Ed. 2005; 44: 6231
• 34h Fischer P, Gruner M, Jäger A, Kataeva O, Metz P. Chem. Eur. J. 2011; 17: 13334
• 34i Germay O, Kumar N, Moore CG, Thomas EJ. Org. Biomol. Chem. 2012; 10: 9709

For fragment syntheses, see:
• 35a Walkup RD, Park G. Tetrahedron Lett. 1988; 29: 5505
• 35b Walkup RD, Kim SW, Wagy SD. J. Org. Chem. 1993; 58: 6486
• 35c Walkup RD, Kim SW. J. Org. Chem. 1994; 59: 3433
• 35d Walkup RD, Kim YS. Tetrahedron Lett. 1995; 36: 3091
• 35e Mavropoulos I, Perlmutter P. Tetrahedron Lett. 1996; 37: 3751
• 35f Arista L, Gruttadauria M, Thomas EJ. Synlett 1997; 627
• 35g Mandville G, Girard C, Bloch R. Tetrahedron: Asymmetry 1997; 8: 3665
• 35h Mandville G, Bloch R. Eur. J. Org. Chem. 1999; 2303
• 35i Solladie G, Salom-Roig XJ, Hanquet G. Tetrahedron Lett. 2000; 41: 551
• 35j Bernsmann H, Hungerhoff B, Fechner R, Fröhlich R, Metz P. Tetrahedron Lett. 2000; 41: 1721
• 35k Calter MA, Bi FC. Org. Lett. 2000; 2: 1529
• 35l Solladie G, Salom-Roig XJ, Hanquet G. Tetrahedron Lett. 2000; 41: 2737
• 35m Bernsmann H, Fröhlich R, Metz P. Tetrahedron Lett. 2000; 41: 4347
• 35n Bernsmann H, Gruner M, Metz P. Tetrahedron Lett. 2000; 41: 7629
• 35o Bernsmann H, Gruner M, Fröhlich R, Metz P. Tetrahedron Lett. 2001; 42: 5377
• 35p Miura A, Takigawa S.-y, Furuya Y, Yokoo Y, Kuwahara S, Kiyota H. Eur. J. Org. Chem. 2008; 4955
• 36a Ren G.-B, Wu Y.-K. Org. Lett. 2009; 11: 5638
• 36b Ren G.-B, Huang Y.-X, Sun Y.-P, Li Z.-H, Wu Y.-K. J. Org. Chem. 2010; 75: 5048
• 36c Ren G.-B, Wu Y.-K. Chin. J. Chem. 2010; 28: 1651
• 37 Nahm S, Weinreb SM. Tetrahedron Lett. 1981; 22: 3815
• 38 Evans DA, Tedrow JS, Shaw JT, Downey CW. J. Am. Chem. Soc. 2002; 124: 392
• 39 Mulzer J, Pietschman C, Schollhorn B, Buschmann J, Luger P. Liebigs Ann. 1995; 1433
• 40a Wu J.-Z, Gao J, Ren G.-B, Zhen Z.-B, Zhang Y.-H, Wu Y.-K. Tetrahedron 2009; 65: 289

For other applications, see:
• 40b Zhang S.-M, Wu Y.-K. Chin. J. Chem. 2011; 29: 2798
• 40c He L, Zhang S.-M, Wu Y.-K, Li Y. Chin. J. Chem. 2011; 29: 2664
• 40d Yan X, Zhang S.-M, Wu Y.-K, Gao P. Org. Biomol. Chem. 2011; 9: 6797
• 40e Jiang P, Zhang S.-M, He L, Wu Y.-K, Li Y. Tetrahedron 2011; 67: 2651
• 40f Chen C.-Y, Zhang S.-M, Wu Y.-K, Gao P. Eur. J. Org. Chem. 2013; 348
• 41 Prashad M, Har D, Kim H.-Y, Repic O. Tetrahedron Lett. 1998; 39: 7067
• 42a Chaudhary K. Org. Lett. 2000; 2: 775
• 42b See also ref. 9c.
• 43a Minami Y, Yoshida K, Azuma R, Nishii M, Inagaki J, Nohara F. Tetrahedron Lett. 1992; 33: 7373
• 43b Ishida T, In Y, Nishii M, Minami Y. Chem. Lett. 1994; 1321
• 44 Hwang EI, Yun BS, Yeo WH, Lee SH, Moon JS, Kim YK, Lim SJ, Kim SU. J. Microbiol. Biotechnol. 2005; 15: 909. No optical rotation data was given
• 45 Zou Y, Wu Y.-K. Angew. Chem. Int. Ed. 2012; 51: 4968
• 46 Crimmins MT, She J. Synlett 2004; 1371
• 47 Stork G, Zhao K. Tetrahedron Lett. 1989; 30: 287

For several elegant solutions to this type of problem, see:
• 48a Guz NR, Phillips AJ. Org. Lett. 2002; 4: 2253
• 48b Zhang Y, Sammakia T. Org. Lett. 2004; 6: 3139
• 48c Crimmins MT, Shamszad M. Org. Lett. 2007; 9: 149
• 49 Fuwa H, Sasaki M. Org. Lett. 2010; 12: 584
• 50a Kim WH, Hong SK, Lim SM, Ju M.-A, Jung SK, Kim YW, Jung JH, Kwon MS, Lee E. Angew. Chem. Int. Ed. 2006; 45: 7072
• 50b Kim WH, Hong SK, Lim SM, Ju M.-A, Jung SK, Kim YW, Jung JH, Kwon MS, Lee E. Tetrahedron 2007; 63: 9784

For fragment syntheses, see:
• 50c Jiang W, Lantrip DA, Fuchs PL. Org. Lett. 2000; 2: 2181
• 51 This incorrect specific rotation datum was the only one (with concentration and solvent specified) available in the major online databases, such as SciFinder (http://www.cas.org/products/scifinder) (accessed June 10, 2013) and Reaxys (http://www.elsevier.com/online-tools/reaxys) (accessed June 10, 2013).
• 52 Nishii M. JP 02009382, 1990 ; Chem. Abstr. 1990, 113, 103380
• 53 Optical rotations measured in different solvents may be misleading; for example, data of opposite signs were found with pamamycin 621A (see ref. 36a and 36b)