Expedient Route to the functionalized calyciphylline A-type skeleton via a Michael addition-RCM strategy

Filippo Sladojevich; Iacovos N Michaelides; Darses Benjamin; John W Ward; Darren J Dixon

doi:10.1021/ol202000w

Expedient Route to the functionalized calyciphylline A-type skeleton via a Michael addition-RCM strategy

Org Lett. 2011 Oct 7;13(19):5132-5. doi: 10.1021/ol202000w. Epub 2011 Sep 7.

Authors

Filippo Sladojevich¹, Iacovos N Michaelides, Darses Benjamin, John W Ward, Darren J Dixon

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

PMID: 21899283
DOI: 10.1021/ol202000w

Abstract

An efficient, robust, and scalable strategy to access the functionalized core of calyciphylline A-type alkaloids has been developed starting from commercially available 3-methylanisole. Key features of this approach are an intramolecular Michael addition/allylation sequence and a ring-closing metathesis step.

Publication types

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

MeSH terms

Anisoles / chemistry
Models, Molecular
Molecular Structure
Polycyclic Compounds / chemical synthesis*

Substances

Anisoles
Polycyclic Compounds
calyciphylline A