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-00000083.xml
Synlett 2004(8): 1437-1439
DOI: 10.1055/s-2004-825624
DOI: 10.1055/s-2004-825624
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Membranacin
Weitere Informationen
Received
17 March 2004
Publikationsdatum:
08. Juni 2004 (online)
Publikationsverlauf
Publikationsdatum:
08. Juni 2004 (online)
![](https://www.thieme-connect.de/media/synlett/200408/lookinside/thumbnails/10.1055-s-2004-825624-1.jpg)
Abstract
The synthesis of the Annonaceous acetogenin membranacin (2) has been achieved, using transition metal-oxo and transition metal-peroxy species in the key steps.
Key words
oxidations - asymmetric synthesis - natural products - manganese - total synthesis
- For recent reviews:
-
1a
Zafra-Polo MC.Figadère B.Gallardo T.Tormo JR.Cortes D. Phytochemistry 1998, 48: 1087 -
1b
Alali FQ.Liu XX.McLaughlin JL. J. Nat. Prod. 1999, 62: 504 - For reviews of acetogenin synthesis see ref. 1 and:
-
2a
Hoppe R.Scharf HD. Synthesis 1995, 1447 -
2b
Figadère B.Cavé A. In Studies in Natural Products Chemistry Vol. 18:Rahman AU. Elsevier Science; Amsterdam: 1996. p.193-227 -
2c
Marshall JA.Hinkle KW.Hagedorn CE. Isr. J. Chem. 1997, 37: 97 -
2d
Casiraghi G.Zanardi F.Battistini L.Rassu G.Appendino G. Chemtracts 1998, 11: 803 - For selected recent approaches to the synthesis of acetogenins:
-
3a
Baurle S.Hoppen S.Koert U. Angew. Chem. Int. Ed. 1999, 38: 1263 -
3b
Marshall JA.Piettre A.Paige MA.Valeriote F. J. Org. Chem. 2003, 68: 1771 -
3c
Sinha SC.Sinha A.Sinha SC.Keinan E. J. Am. Chem. Soc. 1998, 120: 4017 -
3d
Trost BM.Calkins TL.Bochet CG. Angew. Chem., Int. Ed. Engl. 1997, 36: 2632 -
3e
Hanessian S.Grillo TA. J. Org. Chem. 1998, 63: 1049 -
3f
Kuriyama W.Ishigami K.Kitahara T. Heterocycles 1999, 50: 981 -
3g
Yu Q.Wu YK.Ding H.Wu YL. J. Chem. Soc., Perkin Trans. 1 1999, 1183 -
3h
Ruan ZM.Dabideen D.Blumenstein M.Mootoo DR. Tetrahedron 2000, 56: 9203 -
3i
Zanardi F.Battistini L.Rassu G.Auzzas L.Pinna L.Marzocchi L.Acquotti D.Casiraghi G. J. Org. Chem. 2000, 65: 2048 -
3j
Hu TS.Yu Q.Wu YL.Wu YK. J. Org. Chem. 2001, 66: 853 -
3k
Dixon DJ.Ley SV.Reynolds DJ. Chem.-Eur. J. 2002, 8: 1621 -
3l
Cecil ARL.Brown RCD. Org. Lett. 2002, 4: 3715 - 4
Brown RCD.Hughes RM.Keily J.Kenney A. Chem. Commun. 2000, 1735 -
5a
Saez J.Sahpaz S.Villaescusa L.Hocquemiller R.Cave A.Cortes D. J. Nat. Prod. 1993, 56: 351 -
5b
Gonzalez MC.Lavaud C.Gallardo T.Zafra-Polo MC.Cortes D. Tetrahedron 1998, 54: 6079 - For examples of the oxidative cyclisation of 1,5-dienes using metal-oxo species see ref. 3 and:
-
6a (MnO4
-):
Klein E.Rojahn W. Tetrahedron 1979, 21: 2353 -
6b
Walba DM.Przybyla CA.Walker CBJ. J. Am. Chem. Soc. 1990, 112: 5624 -
6c
Kocienski PJ.Brown RCD.Pommier A.Procter M.Schmidt B. J. Chem. Soc., Perkin Trans. 1 1998, 9 -
6d Ruthenium:
Carlsen PHJ.Katsuki T.Martin VS.Sharpless KB. J. Org. Chem. 1981, 46: 3936 -
6e
Albarella L.Musumeci D.Sica D. Eur. J. Org. Chem. 2001, 997 -
6f
Bifulco G.Caserta T.Gomez-Paloma L.Piccialli V. Tetrahedron Lett. 2003, 44: 3429 -
6g OsO4:
de Champdore M.Lasalvia M.Piccialli V. Tetrahedron Lett. 1998, 39: 9781 -
6h
Donohoe TJ.Butterworth S. Angew. Chem. Int. Ed. 2003, 42: 978 - 7
Brown RCD.Bataille CJ.Hughes RM.Kenney A.Luker TJ. J. Org. Chem. 2002, 67: 8079 - 9
Saito S.Ishikawa T.Kuroda A.Koga K.Moriwake T. Tetrahedron 1992, 48: 4067 - 10
Hoye TR.Tan L. Tetrahedron Lett. 1995, 36: 1981 - 11
Trost BM.Müller TJJ.Martinez J. J. Am. Chem. Soc. 1995, 117: 1888
References
A single diastereoisomer 3 was isolated from the reaction mixture, although oxidative cyclisation of similar substrates has been found to proceed with a diastereoselectivity of approximately 6:1.