Convergent syntheses of 3,6-dihydroxydec-4-enolides

Jonathan C Killen; Lorraine C Axford; Sarah E Newberry; Thomas J Simpson; Christine L Willis

doi:10.1021/ol3018566

Convergent syntheses of 3,6-dihydroxydec-4-enolides

Org Lett. 2012 Aug 17;14(16):4194-7. doi: 10.1021/ol3018566. Epub 2012 Jul 31.

Authors

Jonathan C Killen¹, Lorraine C Axford, Sarah E Newberry, Thomas J Simpson, Christine L Willis

Affiliation

¹ School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.

PMID: 22849633
DOI: 10.1021/ol3018566

Abstract

The total syntheses of the 3,6-dihydroxydecanolide from Cordyceps militaris and the novel C-3 epimer are reported using a diastereoselective Nozaki-Hiyama-Kishi reaction in the key cyclization to generate the 6R stereocenter.

Publication types

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

MeSH terms

Biological Products / chemical synthesis*
Biological Products / chemistry
Biological Products / isolation & purification
Cordyceps / chemistry*
Cyclization
Lactones / chemical synthesis*
Lactones / chemistry
Lactones / isolation & purification
Molecular Structure
Stereoisomerism

Substances

3,6-dihydroxydecanolide
Biological Products
Lactones