Chemoenzymatic synthesis of the enantiomer of 4,12-dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of Stereum purpureum

Ping Lan; Martin G Banwell; Anthony C Willis

doi:10.1021/ol5034817

Chemoenzymatic synthesis of the enantiomer of 4,12-dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of Stereum purpureum

Org Lett. 2015 Jan 2;17(1):166-9. doi: 10.1021/ol5034817. Epub 2014 Dec 18.

Authors

Ping Lan¹, Martin G Banwell, Anthony C Willis

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.

PMID: 25522001
DOI: 10.1021/ol5034817

Abstract

Compound ent-1 has been prepared by engaging a derivative of the enantiomerically enriched and microbially derived cis-1,2-dihydrocatechol 6 in an intramolecular Diels-Alder reaction, elaboration of the adduct so-formed to the cyclopentannulated bicyclo[2.2.2]octenone 3, and photochemical rearrangement of this to the cyclobutanone 2. By such means it has been established that 4,12-dihydroxysterpurene (1) is not the structure of the natural product isolated by Xie and co-workers from a culture broth of Stereum purpureum.

Publication types

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

MeSH terms

Agaricales / chemistry*
Biological Products / chemical synthesis*
Biological Products / chemistry
Cycloaddition Reaction
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Sorbus / microbiology
Stereoisomerism

Substances

4,12-dihydroxysterpurene
Biological Products
Sesquiterpenes
sterpurene