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

Matthew G Lloyd; Mariantonietta D'Acunto; Richard J K Taylor; William P Unsworth

doi:10.1039/c5ob02579f

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

Org Biomol Chem. 2016 Feb 7;14(5):1641-5. doi: 10.1039/c5ob02579f.

Authors

Matthew G Lloyd¹, Mariantonietta D'Acunto², Richard J K Taylor¹, William P Unsworth¹

Affiliations

¹ Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK. [email protected] [email protected].
² University of Salerno, Department of Chemistry and Biology, Via Giovanni Paolo II, 132, Salerno, 84084 Fisciano, Italy.

PMID: 26695888
DOI: 10.1039/c5ob02579f

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
4-Butyrolactone / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Molecular Structure
Stereoisomerism

Substances

Biological Products
alpha-methylene gamma-butyrolactone
4-Butyrolactone