Total synthesis of (+)-1893B aimed at establishing its stereochemistry

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

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Abstract

The total synthesis of (+)-1893B (2) has been completed. The one-pot ring-opening/cross/ring-closing metathesis of (1S,2S,3S,4R)-2-(t-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene (4) provided (1R,6S,7S,8S)-7-hydroxymethyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene (6) after deblocking. The epoxy-ring opening of an advanced intermediate (1R,6S,7S,8S)-7-[(1S,2S)-1-methoxymethoxy-2,3-epoxypropyl]-8-methyl-9-oxabi cyclo[4.2.1]nona-2,4-diene (11a) with trimethylsilylacetylide, followed by palladium(II)-catalyzed oxidation for construction of the γ-lactone moiety in 2.

Original languageEnglish
Pages (from-to)123-128
Number of pages6
JournalHeterocycles
Volume67
Issue number1
DOIs
Publication statusPublished - 2006 Jan 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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