Helvetica chimica acta

Synthesis of cis??Hedione® and Methyl Jasmonate via Cascade Baylis–Hillman Reaction and Claisen Ortho Ester Rearrangement

C Chapuis, GH BüCHI, H Wüest

Index: Chapuis, Christian; Buechi, George H.; Wueest, Hans Helvetica Chimica Acta, 2005 , vol. 88, # 12 p. 3069 - 3088

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Citation Number: 28

Abstract

Abstract The exocyclically unsaturated conjugated keto esters 10, obtained via a Claisen ortho ester rearrangement of the allylic hydroxy ketones 9, were either directly hydrogenated or partially isomerized into the endocyclically unsaturated tetrasubstituted didehydrojasmonoid intermediates 14, prior to a more selective hydrogenation with Pd/C in cyclohexane to the disubstituted oxocyclopentaneacetates 15 (Scheme 2). The key ...

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