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Synthesis 2011(1): 104-108
DOI: 10.1055/s-0030-1258327
DOI: 10.1055/s-0030-1258327
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Formal Synthesis of Ionomycin Featuring a Permanganate-Mediated Oxidative Cyclisation
Further Information
Received
15 July 2010
Publication Date:
15 November 2010 (online)
Publication History
Publication Date:
15 November 2010 (online)
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
- Supporting Information for this article is available online:
- Supporting Information
- 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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References
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