Second-generation synthesis of azadirachtin: a concise preparation of the propargylic mesylate fragment

Alistair Boyer; Gemma E Veitch; Edith Beckmann; Steven V Ley

doi:10.1002/anie.200805395

Second-generation synthesis of azadirachtin: a concise preparation of the propargylic mesylate fragment

Angew Chem Int Ed Engl. 2009;48(7):1317-20. doi: 10.1002/anie.200805395.

Authors

Alistair Boyer¹, Gemma E Veitch, Edith Beckmann, Steven V Ley

Affiliation

¹ Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.

PMID: 19140148
DOI: 10.1002/anie.200805395

Abstract

A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished (see scheme; Bn = benzyl, Ms = methanesulfonyl, PMB = para-methoxybenzyl, TBDPS = tert-butyldiphenylsilyl). An enantioselective catalytic hetero Diels-Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps.

Publication types

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

MeSH terms

Catalysis
Lactones / chemistry
Limonins / chemical synthesis*
Limonins / chemistry
Mesylates / chemical synthesis
Mesylates / chemistry
Stereoisomerism

Substances

Lactones
Limonins
Mesylates
azadirachtin