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Diastereoselective radical cyclization of bromoacetals: Efficient synthesis of (±)-botryodiplodin

✍ Scribed by Fe´lix Villar; Olivier Andrey; Philippe Renaud

Book ID
104261271
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
191 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereoselective synthesis of (_)-botryodiplodin is presented. The key reaction is a radical cyc|ization of a bromoacetal (Ueno-Stork reaction). The stereogenic acetal center has been used to control the stereoselectivity of the process: the difficulty in controlling the stereochemistry at C(3) of the tetrahydrofuran moiety during the cyclization step has been overcome by a double one-pot reduction procedure starting from agem-dibromide.

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ChemInform Abstract: Diastereoselective
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