Issue 5, 2016
From the journal:

Organic & Biomolecular Chemistry

A selective C–H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products†

Matthew G. Lloyd,a   Mariantonietta D'Acunto,b   Richard J. K. Taylor*a  and  William P. Unsworth*a  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: richard.taylor@york.ac.uk, william.unsworth@york.ac.uk

b University of Salerno, Department of Chemistry and Biology, Via Giovanni Paolo II, 132, Salerno, 84084 Fisciano, Italy

Abstract

A regio- and stereoselective one-pot C–H insertion/olefination protocol has been developed for the late stage installation of α-methylene-γ-butyrolactones into conformationally restricted cyclohexanol-derivatives. The method has been successfully applied in the total synthesis of eudesmanolide natural product frameworks, including α-cyclocostunolide.

Graphical abstract: A selective C–H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products

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Article information

DOI
https://doi.org/10.1039/C5OB02579F
Article type
Paper
Submitted
16 Dec 2015
Accepted
17 Dec 2015
First published
17 Dec 2015

Org. Biomol. Chem., 2016,14, 1641-1645

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A selective C–H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products

M. G. Lloyd, M. D'Acunto, R. J. K. Taylor and W. P. Unsworth, Org. Biomol. Chem., 2016, 14, 1641 DOI: 10.1039/C5OB02579F

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