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

Date

2015

Authors

Lan, Ping
Banwell, Martin
Willis, Anthony C.

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

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.

Description

Keywords

agaricales, biological products, cycloaddition reaction, molecular structure, nuclear magnetic resonance, sesquiterpenes, sorbus, stereoisomerism, biomolecular

Citation

Source

Organic Letters

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/ol5034817

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