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Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

ABSTRACT: A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.

SUBMITTER: Hoye AT 

PROVIDER: S-EPMC3099051 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

Hoye Adam T AT   Wipf Peter P  

Organic letters 20110421 10

A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented. ...[more]