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Issue 23, 2011
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Concise formal synthesis of (−)-7-deoxyloganinvia N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters

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Abstract

NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β-unsaturated acids provides the cyclopentapyranone core of (−)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (−)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous work on (−)-7-deoxyloganin (1) allowing completion of a formal total synthesis in 10-steps.

Graphical abstract: Concise formal synthesis of (−)-7-deoxyloganinvia N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters

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Article information


Submitted
13 Jun 2011
Accepted
14 Sep 2011
First published
14 Sep 2011

Org. Biomol. Chem., 2011,9, 8182-8189
Article type
Paper

Concise formal synthesis of (−)-7-deoxyloganinvia N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters

L. Candish and D. W. Lupton, Org. Biomol. Chem., 2011, 9, 8182
DOI: 10.1039/C1OB05953J

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