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Regioselective epoxide ring opening. Steroselective synthesis of a tetrahydropyran ring

✍ Scribed by Michelangelo Gruttadauria; Renato Noto; Serena Riela

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 339 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350414

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✦ Synopsis

Abstract

The stereoselective synthesis of a 2‐substituted tetrahydropyran with adjacent alkoxy‐bearing stereogenic centre is described. The key steps of this synthesis were the stereoselective epoxidation of an allylic alcohol and the regioselective epoxide ring opening by lithium aluminum hydride. The regio and stereoselective synthesis of a trihydroxyselenide and a trihydroxysulfide is also described. The latter compounds are not suitable for cyclization to tetrahydrofuran ring.

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