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

J Org Chem. 2014 Mar 21;79(6):2564-73. doi: 10.1021/jo500027k. Epub 2014 Feb 27.

Authors

Henry P Pepper¹, Stephen J Tulip, Yuji Nakano, Jonathan H George

Affiliation

¹ School of Chemistry & Physics, University of Adelaide , Adelaide 5005, South Australia, Australia.

PMID: 24575789
DOI: 10.1021/jo500027k

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.

Publication types

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

MeSH terms

Benzophenones / chemical synthesis*
Benzophenones / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Biomimetics
Cyclization
Molecular Structure
Oxidation-Reduction
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry
Stereoisomerism

Substances

Benzophenones
Biological Products
Polycyclic Compounds
doitunggarcinone A
garcibracteatone