Formal total synthesis of (-)-apicularen a by a strategy based on ring-closing metathesis and transannular cyclization

Young Hee Jung, Young Ju Kim, Jieun Lee, Jinsung Tae

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Abstract

A formal synthesis of (-)-apicularen A, a potent antitumor agent with unique biological properties, has been completed in a 15-step sequence starting from a known, enantiomerically pure hydroxyepoxide, which was generated by using the Jacobsen hydrolytic-kinetic-resolution methodology. The 12-membered macrocyclic lactone in the target was constructed by ring-closing metathesis, and the frans-tetrahydropyran ring system was created through the transannular etherification of a hydroxyalkene.

Original languageEnglish
Pages (from-to)656-661
Number of pages6
JournalChemistry - An Asian Journal
Volume2
Issue number5
DOIs
Publication statusPublished - 2007 Jul 2

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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