First total synthesis of rhodexin A

Michael E Jung; Dongwon Yoo

doi:10.1021/ol200796r

First total synthesis of rhodexin A

Org Lett. 2011 May 20;13(10):2698-701. doi: 10.1021/ol200796r. Epub 2011 Apr 25.

Authors

Michael E Jung¹, Dongwon Yoo

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States. jung@chem.ucla.edu

PMID: 21517087
DOI: 10.1021/ol200796r

Abstract

An efficient total synthesis of rhodexin A (1) is reported. An initial inverse-electron-demand Diels-Alder reaction of the acyldiene 6 with the silyl enol ether 7 gave the cycloadduct 8 with the required 4 contiguous stereocenters in a single step. This compound was then transformed into the tetracyclic enone 16, which was converted to rhodexin A (1).

Publication types

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

MeSH terms

Antineoplastic Agents
Cardiac Glycosides / chemical synthesis*
Cardiac Glycosides / chemistry
Cardiac Glycosides / pharmacology
Cyclization
Glycosides
Lactones
Molecular Structure
Stereoisomerism

Substances

Antineoplastic Agents
Cardiac Glycosides
Glycosides
Lactones
rhodexin A