Exaltone®(= Cyclopentadecanone) from Isomuscone®(= Cyclohexadecanone), a One??C??Atom Ring??Contraction Methodology via a Stereospecific Favorskii …

…, F Robvieux, C Cantatore, C Saint??Léger…

文献索引：Chapuis, Christian; Robvieux, Fabrice; Cantatore, Carole; Saint-Leger, Christine; Maggi, Laurent Helvetica Chimica Acta, 2012 , vol. 95, # 3 p. 428 - 447

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被引用次数: 2

摘要

Abstract Treatment of cyclohexadecanone (1g; with I 2 (2.2 mol-euqiv.) and KOH in MeOH) furnished the unsaturated (Z)-ester 2g in 83% yield, via a stereospecific Favorskii rearrangement (Scheme 1). Further treatment with 3-chloroperbenzoic acid (m-CPBA) afforded the unreported epoxy ester 3g (88% yield), which was cleaved in 33% yield to Exaltone®(= cyclopentadecanone; 1f) with NaOH in MeOH/H 2 O and then HCl at 65. This ...

~89%

~32%

~48%

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