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Issue 28, 2015
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A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1

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Abstract

A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau–Demjanov reaction. Starting from readily available (R)-(−)-carvone, this robust sequence is available on a deca-gram scale and uses flow chemistry for the initial epoxidation reaction. The stereochemistry of the addition of two nucleophiles to the carbonyl group of (R)-(−)-carvone has been determined by X-ray diffraction studies and chemical correlation.

Graphical abstract: A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1

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Article information


Submitted
16 Mar 2015
Accepted
06 May 2015
First published
08 May 2015

This article is Open Access

Org. Biomol. Chem., 2015,13, 7633-7642
Article type
Paper
Author version available

A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1

L. D. C. Alves, A. L. Desiderá, K. T. de Oliveira, S. Newton, S. V. Ley and T. J. Brocksom, Org. Biomol. Chem., 2015, 13, 7633
DOI: 10.1039/C5OB00525F

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