Tandem Diels-Alder/fragmentation approach to the synthesis of eleutherobin

Jeffrey D Winkler; Kevin J Quinn; Colin H MacKinnon; Steven D Hiscock; Emily C McLaughlin

doi:10.1021/ol0345226

Tandem Diels-Alder/fragmentation approach to the synthesis of eleutherobin

Org Lett. 2003 May 15;5(10):1805-8. doi: 10.1021/ol0345226.

Authors

Jeffrey D Winkler¹, Kevin J Quinn, Colin H MacKinnon, Steven D Hiscock, Emily C McLaughlin

Affiliation

¹ Department of Chemistry, The University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. [email protected]

PMID: 12735782
DOI: 10.1021/ol0345226

Abstract

[reaction: see text] A synthesis of 28, the carbon framework of the eleutherobin aglycone, is reported in a 15-step sequence from readily available starting materials. The tandem Diels-Alder reaction of 6 and 7 to produce 18, in which three new rings and six new stereocenters are formed, is a key step in the reaction sequence.

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Anthozoa / chemistry
Antineoplastic Agents / chemical synthesis*
Cyclization
Diterpenes*
Indicators and Reagents
Molecular Conformation

Substances

Alkaloids
Antineoplastic Agents
Diterpenes
Indicators and Reagents
eleutherobin