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Issue 28, 2014
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β-Hydroxy-γ-lactones as nucleophiles in the Nicholas reaction for the synthesis of oxepene rings. Enantioselective formal synthesis of (−)-isolaurepinnacin and (+)-rogioloxepane A

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Abstract

The enantioselective formal synthesis of (−)-isolaurepinnacin and (+)-rogioloxepane A has been achieved. The key steps are an intermolecular Nicholas reaction with a β-hydroxy-γ-lactone as the nucleophile, to form branched linear ethers, and an olefin ring-closing metathesis to obtain the oxepene core.

Graphical abstract: β-Hydroxy-γ-lactones as nucleophiles in the Nicholas reaction for the synthesis of oxepene rings. Enantioselective formal synthesis of (−)-isolaurepinnacin and (+)-rogioloxepane A

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Article information


Submitted
16 Jan 2014
Accepted
11 Feb 2014
First published
12 Feb 2014

Chem. Commun., 2014,50, 3685-3688
Article type
Communication
Author version available

β-Hydroxy-γ-lactones as nucleophiles in the Nicholas reaction for the synthesis of oxepene rings. Enantioselective formal synthesis of (−)-isolaurepinnacin and (+)-rogioloxepane A

J. Rodríguez-López, N. Ortega, V. S. Martín and T. Martín, Chem. Commun., 2014, 50, 3685
DOI: 10.1039/C4CC00389F

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