Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B

The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2' cyclization to construct the central bicyclo(2.2.2) nucleus. A synthetic route to C-10-epibrevianamide A is also described. A synthetic sa...

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Bibliographic Details
Published in:	Journal of the American Chemical Society Vol. 112; no. 2; pp. 808 - 821
Main Authors:	Williams, Robert M, Glinka, Tomasz, Kwast, Ewa, Coffman, Hazel, Stille, James K
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 1990
Subjects:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties Intramolecular reaction Angular nitrogen heterocycle Nitrogen heterocycle Lactam Tetracyclic compound Spiran Total synthesis Cyclization Asymmetric reaction Bicyclic compound SN2' mechanism Aromatic compound Enantiomer(-)
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Summary:	The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2' cyclization to construct the central bicyclo(2.2.2) nucleus. A synthetic route to C-10-epibrevianamide A is also described. A synthetic sample of a shunt metabolite proposed by Birch in 1972 has been prepared and its oxidation chemistry in the context of the proposed biosynthetic schemes is discussed.
Bibliography:	ark:/67375/TPS-25V258SV-D istex:7F3186A6D2E58C22C30A04AFB4540F3D7E8E0270 ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja00158a048