Chemoenzymatic Access to Versatile Epoxyquinol Synthons

Date

2009

Authors

Pinkerton, David
Banwell, Martin
Willis, Anthony

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps Into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their Immediate precursors have been exploited In efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).

Description

Keywords

Keywords: bromoxone; cyclohexene derivative; epiepoformin; epoxide; fused heterocyclic rings; harveynone; hexacyclinol; hydroquinone derivative; panepophenanthrin; phenanthrene derivative; polycyclic hydrocarbon; article; chemistry; conformation; stereoisomerism; s

Citation

Source

Organic Letters

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/ol9016657

Restricted until

2037-12-31