Biomimetic Total Synthesis of (±)-Doitunggarcinone A and (+)-Garcibracteatone

Henry P. Pepper, Stephen J. Tulip, Yuji Nakano, Jonathan H. George

Research output: Contribution to journalArticleResearchpeer-review

24 Citations (Scopus)

Abstract

A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.

Original languageEnglish
Pages (from-to)2564-2573
Number of pages10
JournalThe Journal of Organic Chemistry
Volume79
Issue number6
DOIs
Publication statusPublished - 21 Mar 2014

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