RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(18): 3162-3173
DOI: 10.1055/s-0029-1216939
DOI: 10.1055/s-0029-1216939
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Dibromophakellin, Dibromophakellstatin, and Dibromoagelaspongin via Oxidative Cyclization of Dihydrooroidin Derivatives
Weitere Informationen
Received
1 July 2009
Publikationsdatum:
14. August 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. August 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200918/lookinside/thumbnails/10.1055-s-0029-1216939-1.jpg)
Abstract
A putative biosynthesis proposal for oroidin-derived marine alkaloids serves as a template for developing a biomimetic strategy for the syntheses of tetracyclic members of the phakellin family of sponge metabolites. Pummerer chemistry triggers the oxidative cyclization of the dihydrooroidin derivative, and dibromophakellin, dibromophakellstatin, and dibromoagelaspongin all can be accessed efficiently via this strategy.
Key words
oxidative cyclization - Pummerer - marine alkaloid
-
1a
Hoffmann H.Lindel T. Synthesis 2003, 1753 -
1b
Jacquot DEN.Lindel T. Curr. Org. Chem. 2005, 9: 1551 -
1c
Weinreb SM. Nat. Prod. Rep. 2007, 24: 931 -
1d
Pedpradab S. Ph.D. Thesis Heinrich-Heine Universität; Germany: 2005. - 2
Faulkner DJ.Andersen RJ. The Sea Vol. 5: Wiley; New York: 1974. p.679-714 - 3
Sharma G.Magdoff-Fairchild B. J. Org. Chem. 1977, 42: 4118 - 4
Al Mourabit A.Potier P. Eur. J. Org. Chem. 2001, 237 - 6
Büchi G.Foley LH. J. Am. Chem. Soc. 1982, 104: 1776 - 7
Wiese KJ.Yakushijin K.Horne DA. Tetrahedron Lett. 2002, 43: 5135 - 8
Poverlein C.Breckle G.Lindel T. Org. Lett. 2006, 8: 819 - 9
Barrios Sosa AC. .Horne DA. Org. Lett. 2000, 2: 3443 - 10
Fedoreyev SA.Ilyin SG.Utkina NK.Maximov OB.Reshetnyak MV.Antipin MY.Struchkov YT. Tetrahedron 1989, 45: 3487 - 11
Sunazuka T.Shirahata T.Tsuchiya S.Hirose T.Mori R.Harigaya Y.Kuwajima I.Omura S. Org. Lett. 2005, 7: 941 - 12
Olofson AS. Ph.D. Thesis Columbia University; USA: 1998. - 13
Picon S.Dau ETH.Martin M.-T.Retailleau P.Zaparucha A.Al-Mourabit A. Org. Lett. 2009, 11: 2523 -
14a
Buchanan MS.Carroll AR.Quinn RJ. Tetrahedron Lett. 2007, 48: 4573 -
14b
Grube A.Köck M. Angew. Chem. Int. Ed. 2007, 46: 2320 -
14c
Kobayashi H.Kitamura K.Nagai K.Nakao Y.Fusetani N.van Soest RWM.Matsunaga S. Tetrahedron Lett. 2007, 48: 2127 -
14d
Urban S.de Almeida Leone P.Carroll AR.Fechner GA.Smith J.Hooper JNA.Quinn RJ. J. Org. Chem. 1999, 64: 731 - 15
Feldman KS. Tetrahedron 2006, 62: 5003 -
16a
Feldman KS.Vidulova DB. Org. Lett. 2004, 6: 1869 -
16b
Feldman KS.Karatjas AG. Org. Lett. 2004, 6: 2849 -
16c
Feldman KS.Vidulova DB. Tetrahedron Lett. 2004, 45: 5035 -
16d
Feldman KS.Vidulova DB.Karatjas AG. J. Org. Chem. 2005, 70: 6429 - 17
Feldman KS.Karatjas AG. Org. Lett. 2006, 8: 4137 -
18a
Feldman KS.Skoumbourdis AP. Org. Lett. 2005, 7: 929 -
18b
Feldman KS.Skoumbourdis AP.Fodor MD. J. Org. Chem. 2007, 72: 8076 -
19a
Lipshutz BH.Huff B.Hagen W. Tetrahedron Lett. 1988, 29: 3411 -
19b
Vollinga RC.Menge WMPB.Timmerman H. Recl. Trav. Chim. Pays-Bas 1993, 112: 123 - 20
Chadwick DJ.Ngochindo RI. J. Chem. Soc., Perkin Trans. 1 1984, 481 -
21a
Motherwell WB.Greaney MF.Edmunds JJ.Steed JW. J. Chem. Soc., Perkin Trans. 1 2002, 2816 -
21b
Tamura Y.Yakura T.Shirouchi Y.Haruta J.-i. Chem. Pharm. Bull. 1986, 34: 1061 -
21c
Wang H.-M.Lin M.-C.Chen L.-C. Heterocycles 1994, 38: 1519 - 22
Zhdankin VV.Crittell CM.Stang PJ.Zefirov NS. Tetrahedron Lett. 1990, 31: 4821 -
23a
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
23b
Stang PJ. J. Org. Chem. 2003, 68: 2997 -
23c
Knorr R. Chem. Rev. 2004, 104: 3795 -
24a
Tanino H.Nakata T.Kaneka T.Kishi Y. J. Am. Chem. Soc. 1977, 99: 2818 -
24b
Jacobi PA.Martinelli MJ.Slovenko P. J. Am. Chem. Soc. 1984, 106: 5594 -
25a
Feldman KS.Fodor MD. J. Am. Chem. Soc. 2008, 130: 14964 -
25b
Feldman KS.Fodor MD. J. Org. Chem. 2009, 74: 3449 -
26a
Saito S.Sato Y.Ohwada T.Shudo K. J. Am. Chem. Soc. 1994, 116: 2312 -
26b
Yokoyama A.Ohwada T.Shudo K. J. Org. Chem. 1999, 64: 611 -
27a
Du H.He Y.Sivappa R.Lovely CJ. Synlett 2006, 965 -
27b
Sivappa R.Koswatta P.Lovely CJ. Tetrahedron Lett. 2007, 48: 5771 -
27c
O’Malley DP.Li K.Maue M.Zografos A.Baran PS. J. Am. Chem. Soc. 2007, 129: 4762 - 28
Olofson A.Yakushijin K.Horne DA. J. Org. Chem. 1998, 63: 1248 -
29a
Bell AS.Campbell SF.Morris DS.Roberts DA.Stefaniak MH. J. Med. Chem. 1989, 32: 1552 -
29b
Marsh SJ.Kartha KPR.Field RA. Synlett 2003, 1376 -
30a
Meketa ML.Weinreb SM. Org. Lett. 2006, 8: 1443 -
30b
Chauviere G.Bouteille B.Enanga B.de Albuquerque C.Croft SL.Dumas M.Perie J. J. Med. Chem. 2003, 46: 427 -
30c
Bierer DE.O’Connell JF.Parquette FR.Thompson CM.Rapoport H. J. Org. Chem. 1992, 57: 1390 -
30d
Ronne E.Grivas S.Olsson K. Acta Chem. Scand. 1994, 48: 823 - 31
Kita Y.Shibata N.Yoshida N.Tohjo T. Tetrahedron Lett. 1991, 32: 2375 - 32
Lu J.Tan X.Chen C. J. Am. Chem. Soc. 2007, 129: 7768 -
33a
Poullennec KG.Romo D. J. Am. Chem. Soc. 2003, 125: 6344 -
33b
Chung R.Yu E.Incarvito CD.Austin DJ. Org. Lett. 2004, 6: 3881 -
33c
Jacquot DEN.Zöllinger M.Lindel T. Angew. Chem. Int. Ed. 2005, 44: 2295 -
33d
Zöllinger M.Mayer P.Lindel T. J. Org. Chem. 2006, 71: 9431 -
33e
Zöllinger M.Mayer P.Lindel T. Synlett 2007, 2756 -
33f
Imaoka T.Iwamoto O.Noguchi K.-i.Nagasawa K. Angew. Chem. Int. Ed. 2009, 48: 3799
References
Hartree-Fock 6-31G**/MP2 calculations using Spartan 04 on the model systems i and ii.