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Synlett 2010(18): 2747-2750  
DOI: 10.1055/s-0030-1258995
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Sclareolide Based on a Cyclic Enol Ether Ring Contraction Induced by Peroxy Acids

Juan M. Castro, Sofía Salido, Adolfo Sánchez, Joaquín Altarejos*
Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
Fax: +34(953)211876; e-Mail: jaltare@ujaen.es;
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Publication History

Received 1 July 2010
Publication Date:
08 October 2010 (online)

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Abstract

(+)-Sclareolide has been synthesised from (+)-sclareol oxide in one step in high yield, by treatment with peroxy acids under very mild conditions. The reaction pathway does not follow the usual oxidative cleavage of the double bond of (+)-sclareol oxide, but the key intermediate is a five-membered ring hemiketal. The direct conversion of a six-membered cyclic enol ether into a γ-lactone is described for the first time.

Key words

cyclic enol ethers - γ-lactones - ring contraction - oxidative rearrangement - peroxy acids

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30

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