Total Synthesis of Rhazinilam: Axial to Point Chirality Transfer in an Enantiospecific Pd-Catalyzed Transannular Cyclization

A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.

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Bibliographic Details
Published in:Organic letters 2010-10, Vol.12 (19), p.4224-4227
Main Authors: Gu, Zhenhua, Zakarian, Armen
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Biological Products - chemical synthesis
Catalysis
Cyclization
Halogenation
Indolizines - chemical synthesis
Lactams - chemical synthesis
Macrocyclic Compounds - chemical synthesis
Molecular Structure
Palladium - chemistry
Stereoisomerism
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Description
Summary:A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101523z