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An easy route to 11-hydroxy-eudesmanolides. Synthesis of (±) decipienin A

✍ Scribed by F. Javier Moreno-Dorado; Francisco M. Guerra; F. Javier Aladro; Jesús M. Bustamante; Zacarías D. Jorge; Guillermo M. Massanet

Book ID
104209417
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
895 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The preparation of 1 l-hydroxy-eudesmanolides with the stereochemistry found in the Umbelliferae family of plants is described. The decalin system of the eudesmane skeleton is produced by the addition of 5-methyl-2furyllithium to 3-ethoxycyclohex-2-enone and acidic treatment of the resulting adduct. The stereochemistry of the decalones obtained by this method has been corrected. The a-hydroxy-7-1actone moiety is obtained by condensation of the appropriate decalone with methyl pyruvate and subsequent reduction under Luche conditions. The usefulness of this procedure has been proven in the synthesis of decipienin A.

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