Palladium-catalyzed Transformations of Salvinorin A, a Neoclerodane Diterpene from Salvia Divinorum

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2013 Nov 20

PMID 24246026

Citations 7

Authors

Andrew P Riley

Victor W Day

Hernan A Navarro

Thomas E Prisinzano

Affiliations

Soon will be listed here.

Abstract

Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki-Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers.

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