Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Shuichi Hagihara, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

Original languageEnglish
Pages (from-to)257-262
Number of pages6
JournalJournal of Antibiotics
Volume71
Issue number2
DOIs
Publication statusPublished - 2018 Feb 1

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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