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Synthesis of yomogin using a telescoped alpha-methylene-gamma-butyrolactone annelation procedure

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JournalTetrahedron Letters
DatePublished - 2 Feb 2011
Issue number5
Volume52
Number of pages4
Pages (from-to)561-564
Original languageEnglish

Abstract

A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

    Research areas

  • SESQUITERPENE LACTONES, ARTEMISIA-PRINCEPS, CELLS, EUDESMANOLIDES, TERPENOIDS, INDUCTION

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