9-Membered Carbocycle Formation: Development of Distinct Friedel-Crafts Cyclizations and Application to a Scalable Total Synthesis of (±)-caraphenol A

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2014 Mar 29

PMID 24677499

Citations 14

Authors

Nathan E Wright

Scott A Snyder

Affiliations

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Abstract

Explorations into a series of different approaches for 9-membered carbocycle formation have afforded the first reported example of a 9-exo-dig ring closure via a Au(III)-promoted reaction between an alkyne and an aryl ring as well as several additional, unique Friedel-Crafts-type cyclizations. Analyses of the factors leading to the success of these transformations are provided, with the application of one of the developed 9-membered ring closures affording an efficient and scalable synthesis of the bioactive resveratrol trimer caraphenol A. That synthesis proceeded with an average yield of 89% per step (7.8% overall yield) and has provided access to more than 600 mg of the target molecule.

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