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 - Jan 1 1980

Fingerprint

Palladium
Biological Products
Zearalenone
Nandrolone
Thioctic Acid
Nucleophiles
Macrolides
Ketones
Steroids
Alcohols
Oxidation
Acids
1,3-butadiene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

A New Synthetic Method for Natural Products Using Butadiene Telomers Obtained by Palladium-catalyzed Telomerization. / Tsuji, Jiro; Takahashi, Takashi; Shimizu, Isao; Nagashima, Hideo.

In: Journal of Synthetic Organic Chemistry, Japan, Vol. 38, No. 3, 01.01.1980, p. 219-233.

Research output: Contribution to journalArticle

@article{8198da53e72a4363982eb5622caed397,
title = "A New Synthetic Method for Natural Products Using Butadiene Telomers Obtained by Palladium-catalyzed Telomerization",
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.",
author = "Jiro Tsuji and Takashi Takahashi and Isao Shimizu and Hideo Nagashima",
year = "1980",
month = "1",
day = "1",
doi = "10.5059/yukigoseikyokaishi.38.219",
language = "English",
volume = "38",
pages = "219--233",
journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",
issn = "0037-9980",
publisher = "社団法人 有機合成化学協会",
number = "3",

}

TY - JOUR

T1 - A New Synthetic Method for Natural Products Using Butadiene Telomers Obtained by Palladium-catalyzed Telomerization

AU - Tsuji, Jiro

AU - Takahashi, Takashi

AU - Shimizu, Isao

AU - Nagashima, Hideo

PY - 1980/1/1

Y1 - 1980/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85007903368&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85007903368&partnerID=8YFLogxK

U2 - 10.5059/yukigoseikyokaishi.38.219

DO - 10.5059/yukigoseikyokaishi.38.219

M3 - Article

AN - SCOPUS:85007903368

VL - 38

SP - 219

EP - 233

JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

SN - 0037-9980

IS - 3

ER -