Towards the total synthesis of calyculin C: Preparation of the C9-C25 spiroketal-dipropionate unit

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Abstract

An asymmetric synthesis of the C9 –C25 spiroketal fragment of calyculin C is described. Key steps include two crotylation reactions using successively Brown’s reagent and (Z)-crotyltrifluorosilane for the formation of the anti, anti, anti stereotetrad, ynone formation by a Pd-catalyzed coupling of a thiol ester with a terminal alkyne and a double intramolecular hetero-Michael addition for the stereoselective construction of the spiroketal framework.

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Original languageEnglish
Pages (from-to)4364-4373
JournalORGANIC AND BIOMOLECULAR CHEMISTRY
Volume8
Issue number19
Publication statusPublished - 2010
MoE publication typeA1 Journal article-refereed

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