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/TiCl4and 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
DOIs
Publication statusPublished - Oct 1 1989
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective Reduction of Bicyclic Ketals. A New, Enantioselective Synthesis of Isolaurepinnacin and Lauthisan Skeletons'. Together they form a unique fingerprint.

  • Cite this