Total syntheses of (+)-1893B and its three diastereomers and evaluation of their biological activities

Hiroyuki Yasui, Kunihiro Hirai, Shun Yamamoto, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The total syntheses of natural (+)-1893B (2) and three other diastereomers 14, 18, and 21 were accomplished. Starting from the sequential metathesis product 5 prepared in turn from a 7-oxanorbornene derivative (+)-4, 2 was synthesized by means of an epoxy-ring opening of 9a with trimethylsilylacetylide followed by Wacker-type oxidation of the resulting alkyne 10 for the construction of the γ-lactone moiety. By applying the same synthetic sequence, three additional diastereomers of 2, 14, 18, and 21 were also synthesized. The biological activities of previously synthesized 1893A (1), 1893B (2), and the diastereomers of 1893B 14, 18, and 21 were investigated.

Original languageEnglish
Pages (from-to)456-463
Number of pages8
JournalJournal of Antibiotics
Volume59
Issue number8
DOIs
Publication statusPublished - 2006 Aug

Keywords

  • Oxabicyclo[4.2.1]nona-2,4-diene
  • Total synthesis
  • γ-lactone

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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