Synlett 2016; 27(01): 61-66
DOI: 10.1055/s-0035-1560814
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© Georg Thieme Verlag Stuttgart · New York

A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Rehmani N. Muhammad
a   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia   eMail: Martin.Banwell@anu.edu.au
,
Alistair G. Draffan
b   Biota Scientific Management Pty Ltd, Melbourne, VIC 3168, Australia
,
Martin G. Banwell*
a   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia   eMail: Martin.Banwell@anu.edu.au
,
Anthony C. Willis
a   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia   eMail: Martin.Banwell@anu.edu.au
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Publikationsverlauf

Received: 01. Oktober 2015

Accepted after revision: 14. Oktober 2015

Publikationsdatum:
05. November 2015 (online)


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Dedicated to Professor Steve Ley on the occasion of his 70th birthday and in appreciation of the inspirational leadership he has provided to the discipline

Abstract

A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels–Alder reaction to establish the octa­hydro-2H-2,4a-ethanonaphthalene core of platencin.

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