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

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Date

2015

Authors

Lan, Ping
Banwell, Martin G.
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

URI

http://hdl.handle.net/1885/13353

Collections

Open Access Research

Source

Organic Letters

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/ol5034817

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