A concise asymmetric synthesis of the ADE fragment of nakadomarin A

Kateri A Ahrendt; Robert M Williams

doi:10.1021/ol048126e

A concise asymmetric synthesis of the ADE fragment of nakadomarin A

Org Lett. 2004 Nov 25;6(24):4539-41. doi: 10.1021/ol048126e.

Authors

Kateri A Ahrendt¹, Robert M Williams

Affiliation

¹ Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, USA.

PMID: 15548070
DOI: 10.1021/ol048126e

Abstract

The ADE fragment of nakadomarin A has been synthesized in nine linear steps from commercial material. The key transformation is an asymmetric azomethine ylide [1,3]-dipolar cycloaddition to establish the AD-spirocyclic system containing three of the four stereocenters of the natural product. [reaction: see text]

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Azo Compounds / chemistry
Carbolines / chemical synthesis*
Spiro Compounds / chemical synthesis

Substances

Azo Compounds
Carbolines
Spiro Compounds
nakadomarin A
azomethane

Abstract

Publication types

MeSH terms

Substances

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