Total synthesis of (±)-aspidophylline A

Liansuo Zu; Ben W Boal; Neil K Garg

doi:10.1021/ja203227q

Total synthesis of (±)-aspidophylline A

J Am Chem Soc. 2011 Jun 15;133(23):8877-9. doi: 10.1021/ja203227q. Epub 2011 May 18.

Authors

Liansuo Zu¹, Ben W Boal, Neil K Garg

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

PMID: 21553860
DOI: 10.1021/ja203227q

Abstract

We report the total synthesis of (±)-aspidophylline A, one of many complex furoindoline-containing alkaloids that has not been synthesized previously. Our route features a number of key transformations, including a Heck cyclization to assemble the [3.3.1]-bicyclic scaffold as well as a late-stage interrupted Fischer indolization to install the furoindoline and construct the natural product's pentacyclic framework.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Stereoisomerism
Substrate Specificity

Substances

Indole Alkaloids