A New Synthetic Method for Natural Products Using Butadiene Telomers Obtained by Palladium-catalyzed Telomerization

Jiro Tsuji, Takashi Takahashi, Isao Shimizu, Hideo Nagashima

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Butadiene telomers, easily prepared by the palladium-catalyzed telomerization of butadiene with various nucleophiles are extremely useful starting materials for natural product syntheses. The following natural products were synthesized in short steps by using several butadiene telomers : Steroid (19-nortestosterone), macrolides (diplodialides, 9-decanolides, lasiodiplodin, zearalenone, recifeiolide, curvularin), Matsutake alcohol, lipoic acid, pellitorin, dihydrojasmone, methyl dihydrojasmonate, muscone, civetone, pyrethrolone, 12-acetoxy-l,3-dodecadiene, royal jelly acids and queen substance. In these syntheses, Wacker type oxidation of terminal double bonds to methyl ketones catalyzed by PdCl2-CuCl is used in key steps.

Original languageEnglish
Pages (from-to)219-233
Number of pages15
JournalJournal of Synthetic Organic Chemistry, Japan
Volume38
Issue number3
DOIs
Publication statusPublished - 1980

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'A New Synthetic Method for Natural Products Using Butadiene Telomers Obtained by Palladium-catalyzed Telomerization'. Together they form a unique fingerprint.

  • Cite this