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Synthesis 2011(1): 104-108  
DOI: 10.1055/s-0030-1258327
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Formal Synthesis of Ionomycin Featuring a Permanganate-Mediated Oxidative Cyclisation

Yingfa Li, John P. Cooksey, Zhanghua Gao, Philip J. Kocieński*, Stephen M. McAteer, Thomas N. Snaddon
The School of Chemistry and the Institute of Process Research and Development, Leeds University, Leeds LS2 9JT, UK
Fax: +44(113)3436401; e-Mail: p.j.kocienski@leeds.ac.uk;
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Publication History

Received 15 July 2010
Publication Date:
15 November 2010 (online)

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Abstract

Key steps in a synthesis of the C17-C32 fragment of iono­mycin are (a) an auxiliary-directed oxidative cyclisation of a diene with potassium permanganate to construct a tetrahydrofuran ring and four stereogenic centres in a single operation, and (b) a chain-appendage reaction featuring the alkylation of an enolsilane by an oxocarbenium ion generated from a 2-phenylsulfonyl-substituted tetrahydrofuran.

Key words

ionomycin - permanganate oxidation - directed reduction - crotylboration - carbocupration

    Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0007th:
  • Primary Data

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The relative and absolute stereochemistry of the lactone 21 was established by a single crystal X-ray analysis of its enantiomer prepared by an analogous route. See the electronic Supporting Information for details