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

4 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

Fingerprint

Guaiane Sesquiterpenes
Phyllanthus
Kidney Neoplasms
Cycloaddition Reaction
Ether
Cell Line
Growth
2,2-dimethyl-1,3-dioxan-5-one
furan
englerin A

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition. / Hagihara, Shuichi; Hanaya, Kengo; Sugai, Takeshi; Shoji, Mitsuru.

In: Journal of Antibiotics, Vol. 71, No. 2, 01.02.2018, p. 257-262.

Research output: Contribution to journalArticle

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