Synlett 2009(10): 1605-1608  
DOI: 10.1055/s-0029-1217339
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Claisen Rearrangement Using Bicyclic 2-[(Z)-Alkenyl]dihydropyran: Stereoselective Synthesis of trans-Substituted Spiro[4.5]decane

Atsuo Nakazaki, Susumu Kobayashi*
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan
Fax: +81(4)71213671; e-Mail: kobayash@rs.noda.tus.ac.jp;
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Publication History

Received 5 March 2009
Publication Date:
02 June 2009 (online)

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Abstract

We report the first example of the Claisen rearrangement in the 2-[(Z)-alkenyl]dihydropyran system yielding spiro[4.5]decane in a trans fashion. This protocol is useful for the synthesis of trans-substituted spiro[4.5]decanes, a potentially useful class of spirocyclic terpenes and alkaloids.

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