Stereoselective total synthesis of garsubellin A

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The stereoselective total synthesis of garsubellin A is described. The total synthesis was achieved through the stereoselective construction of a bicyclo3.3.1nonane derivative via a three-step sequence: intramolecular cyclopropanation, formation of a germinal dimethyl group, and regioselective ring opening of cyclopropane. To complete the total synthesis of garsubellin A, chemo-And stereoselective hydrogenation to generate the C8 stereogenic center is followed by the formation of the fused tetrahydrofuran ring by a regioselective epoxide-opening reaction with C3 ketone, and finally cross metathesis to construct two prenyl groups.

Original languageEnglish
Pages (from-to)141-145
Number of pages5
JournalJournal of Antibiotics
Volume66
Issue number3
DOIs
Publication statusPublished - 2013 Mar

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Hydrogenation
Epoxy Compounds
Ketones
garsubellin A
tetrahydrofuran
cyclopropane
prenyl

Keywords

  • cyclopropanation
  • garsubellin A
  • natural product
  • stereoselective synthesis
  • total synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Stereoselective total synthesis of garsubellin A. / Uwamori, Masahiro; Nakada, Masahisa.

In: Journal of Antibiotics, Vol. 66, No. 3, 03.2013, p. 141-145.

Research output: Contribution to journalArticle

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