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

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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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Stereochemistry
Palladium
Lactones
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of (+)-1893B aimed at establishing its stereochemistry. / Yasui, Hiroyuki; Hirai, Kunihiro; Yamamoto, Shun; Takao, Kenichi; Tadano, Kin ichi.

In: Heterocycles, Vol. 67, No. 1, 01.01.2006, p. 123-128.

Research output: Contribution to journalArticle

Yasui, H, Hirai, K, Yamamoto, S, Takao, K & Tadano, KI 2006, 'Total synthesis of (+)-1893B aimed at establishing its stereochemistry', Heterocycles, vol. 67, no. 1, pp. 123-128. https://doi.org/10.3987/COM-05-S(T)42
Yasui, Hiroyuki ; Hirai, Kunihiro ; Yamamoto, Shun ; Takao, Kenichi ; Tadano, Kin ichi. / Total synthesis of (+)-1893B aimed at establishing its stereochemistry. In: Heterocycles. 2006 ; Vol. 67, No. 1. pp. 123-128.
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