Issue 2, 2013

A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxidescycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A

Abstract

A short and flexible [3+2+1] synthetic strategy was developed for the synthesis of substituted tetrahydropyran-4-ones, featuring [3+2]-cycloaddition of α,β-unsaturated nitrile oxides and alkenes and oxa-Michael cyclization in a 6-endo-trig fashion. The efficiency of this synthetic strategy was further demonstrated by the concise total synthesis of (±)-diospongin A in 8 steps with 20.2% yield.

Graphical abstract: A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A

Supplementary files

Article information

Article type
Communication
Submitted
25 Oct 2012
Accepted
12 Nov 2012
First published
12 Nov 2012

Chem. Commun., 2013,49, 193-195

A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A

H. Yao, J. Ren and R. Tong, Chem. Commun., 2013, 49, 193 DOI: 10.1039/C2CC37772A

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