Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters

Jennifer Peed; Ignacio Periñán Domínguez; Iwan R Davies; Matt Cheeseman; James E Taylor; Gabriele Kociok-Köhn; Steven D Bull

doi:10.1021/ol2012023

Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters

Org Lett. 2011 Jul 15;13(14):3592-5. doi: 10.1021/ol2012023. Epub 2011 Jun 14.

Authors

Jennifer Peed¹, Ignacio Periñán Domínguez, Iwan R Davies, Matt Cheeseman, James E Taylor, Gabriele Kociok-Köhn, Steven D Bull

Affiliation

¹ Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.

PMID: 21671632
DOI: 10.1021/ol2012023

Abstract

A versatile methodology for the asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters has been developed that relies on a series of Evans' aldol, hydroxyl-directed cyclopropanation, methanolysis, and Hg(II) mediated cyclopropane ring-opening reactions for stereocontrol.

Publication types

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

MeSH terms

Chemistry, Organic / methods*
Cyclopropanes / chemistry
Lactones / chemical synthesis*
Lactones / chemistry
Mercury / chemistry
Molecular Structure
Stereoisomerism

Substances

Cyclopropanes
Lactones
prelactone B
Mercury