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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 9
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Original Articles

Synthetic Studies on Jasmonoids (II)1: A New Synthesis Of Methyl dl-Jasmonate

Woo Young Lee Department of Chemistry, Seoul National University, Seoul, 151-742, Korea
,
Se Young Jang Department of Chemistry, Seoul National University, Seoul, 151-742, Korea
,
Mirry Kim Department of Chemistry, Seoul National University, Seoul, 151-742, Korea
&
Oee Sook Park Department of Chemistry, Chungbuk National University, Chungbuk, 306-763, Korea
Pages 1283-1291 | Accepted 05 Dec 1991, Published online: 24 Sep 2006
 
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Abstract

Successive dialkylation of methyl acetoacetate with allylic functions 2 and 5, followed by oxidation, gave an α,β-unsaturated aldehyde 7. Intramolecular Michael addition of 7 to give a cyclopentanone 8, conversion to diester 9, and Krapcho decarbomethoxylation furnished methyl dl-jasmonate.

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