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

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

doi:10.1021/jo500027k

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

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

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-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 language	English
Pages (from-to)	2564-2573
Number of pages	10
Journal	The Journal of Organic Chemistry
Volume	79
Issue number	6
DOIs	https://doi.org/10.1021/jo500027k
Publication status	Published - 21 Mar 2014

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10.1021/jo500027k

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Cite this

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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.",

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