Pericyclic reactions of prenylated naphthoquinones: biomimetic syntheses of mollugin and microphyllaquinone

Jean-Philip Lumb; Dirk Trauner

doi:10.1021/ol052472u

Pericyclic reactions of prenylated naphthoquinones: biomimetic syntheses of mollugin and microphyllaquinone

Org Lett. 2005 Dec 22;7(26):5865-8. doi: 10.1021/ol052472u.

Authors

Jean-Philip Lumb¹, Dirk Trauner

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 16354086
DOI: 10.1021/ol052472u

Abstract

[reaction: see text] A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6pi-electrocyclizations.

Publication types

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

MeSH terms

Cyclization
Molecular Structure
Naphthoquinones / chemical synthesis*
Naphthoquinones / chemistry*
Plants, Medicinal / chemistry
Pyrans / chemical synthesis*
Pyrans / chemistry
Rubia / chemistry
Stereoisomerism

Substances

Naphthoquinones
Pyrans
microphyllaquinone
rubimaillin