Enantioselective Total Synthesis of (+)-Anthecularin

Yusuke Ogura, Shoko Okada, Naoki Mori, Ken Ishigami, Hidenori Watanabe

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

An enantioselective total synthesis of (+)-anthecularin, an antiplasmodial and antitrypanosomal sesquiterpene lactone, has been achieved in 3.9% overall yield through 18 steps from a known dibromo alcohol. The key features of the synthesis include an intramolecular Claisen-type cyclization of a formyl-protected hydroxyl lactone to construct a bicyclic intermediate with a quaternary stereogenic center and a stereocontrolled 1,2-addition of vinyllithium to a methoxyethyl-protected spirocyclic hydroxyl enone to install a tetrasubstituted asymmetric center with excellent diastereoselection. This first enantioselective synthesis of anthecularin enabled the determination of its absolute configuration as 2R, 3R, 4S, 8R.

Original languageEnglish
Pages (from-to)3888-3891
Number of pages4
JournalOrganic letters
Volume20
Issue number13
DOIs
Publication statusPublished - 2018 Jul 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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