Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions

Eric J Tisdale; Chinmay Chowdhury; Binh G Vong; Hongmei Li; Emmanuel A Theodorakis

doi:10.1021/ol017278w

Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions

Org Lett. 2002 Mar 21;4(6):909-12. doi: 10.1021/ol017278w.

Authors

Eric J Tisdale¹, Chinmay Chowdhury, Binh G Vong, Hongmei Li, Emmanuel A Theodorakis

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.

PMID: 11893183
DOI: 10.1021/ol017278w

Abstract

[reaction: see text] Two different routes to the tricyclic core of Garcinia-derived natural products are described. The first approach is based on a tandem Claisen/Diels-Alder rearrangement and delivers the desired lactone 14. The second approach, employing a Wessely oxidation/Diels-Alder protocol, leads to the same caged heterocycle, albeit with modified constitution.

Publication types

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

MeSH terms

Acrylates / chemistry*
Biological Products / chemical synthesis*
Garcinia / chemistry*
Oxidation-Reduction

Substances

Acrylates
Biological Products
acrylic acid

Grants and funding

CA086079/CA/NCI NIH HHS/United States