A highly stereoselective route to medium-ring-sized trans-alkenolides via oxidative fragmentation of bicyclic oxycyclopropane precursors: application to the synthesis of (+)-recifeiolide

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• 作者：Dzmitry M. Zubrytski ; Dzmitry G. Kananovich<sup> ; sup><sup>kananovich82@tut.by" class="auth_mailsup> ; Oleg G. Kulinkovich
• 关键词：Alkenolides ; Cyclopropanols ; Hypervalent iodine compounds ; Stereoselective synthesis ; (+)-Recifeiolide
• 刊名：Tetrahedron
• 出版年：6 May, 2014
• 年：2014
• 卷：70
• 期：18
• 页码：2944-2950
• 全文大小：483 K

文摘

A new approach to the synthesis of medium-ring-sized trans-alkenolides, based on the oxidative fragmentation of a three-carbon ring in hydroxyalkyl substituted bicyclo[n.1.0]alkan-1-ols readily available from 2-alkylidenecycloalkanones, is described. This methodology was applied to the six-step transformation of cyclooctanone to the natural 12-membered trans-alkenolide antibiotic (+)-recifeiolide.