Unified total syntheses of (-)-medicarpin, (-)-sophoracarpan A, and (±)-kushecarpin A with some structural revisions

Zhen-Gao Feng; Wen-Ju Bai; Thomas R R Pettus

doi:10.1002/anie.201408910

Unified total syntheses of (-)-medicarpin, (-)-sophoracarpan A, and (±)-kushecarpin A with some structural revisions

Angew Chem Int Ed Engl. 2015 Feb 2;54(6):1864-7. doi: 10.1002/anie.201408910. Epub 2014 Dec 4.

Authors

Zhen-Gao Feng¹, Wen-Ju Bai, Thomas R R Pettus

Affiliation

¹ Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA, 93106-9510 (USA).

PMID: 25476784
DOI: 10.1002/anie.201408910

Abstract

The total syntheses of medicarpin, sophoracarpan A, and kushecarpin A from a common intermediate are achieved by using ortho- and para-quinone methide chemistry. Additionally, the relative stereochemistry of sophoracarpan A and B have been reassigned.

Keywords: benzopyran acetal; diastereoselective diels-alder; oxidative dearomatization; pterocarpan; quinone methide.

Publication types

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

MeSH terms

Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Pterocarpans / chemical synthesis*
Pterocarpans / chemistry
Stereoisomerism

Substances

Heterocyclic Compounds, 4 or More Rings
Pterocarpans
kushecarpin A
sophoracarpan A
medicarpin