Stereoselective reduction of bicyclic ketals. A new, enantioselective synthesis of isolaurepinnacin and lauthisan skeletons

Hiyoshizo Kotsuki, Yasuyuki Ushio, Isao Kadota, Masamitsu Ochi

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

A general synthetic strategy for constructing seven- and eight-membered cyclic ether derivatives is described. The important feature of this work is a highly stereoselective reduction of bicyclic ketals, i.e., cis-selective reduction with triethylsilane/TiCl4 and trans-selective reduction with diisobutylaluminum hydride (DIBAL). The procedure completed a new and efficient synthesis of isolaurepinnacin and lauthisan skeletons in optically active forms.

Original languageEnglish
Pages (from-to)5153-5161
Number of pages9
JournalJournal of Organic Chemistry
Volume54
Issue number21
Publication statusPublished - 1989
Externally publishedYes

Fingerprint

Cyclic Ethers
Derivatives
lauthisan
isolaurepinnacin
triethylsilane
diisobutylaluminum
titanium tetrachloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective reduction of bicyclic ketals. A new, enantioselective synthesis of isolaurepinnacin and lauthisan skeletons. / Kotsuki, Hiyoshizo; Ushio, Yasuyuki; Kadota, Isao; Ochi, Masamitsu.

In: Journal of Organic Chemistry, Vol. 54, No. 21, 1989, p. 5153-5161.

Research output: Contribution to journalArticle

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