Approaches to the cephalotaxine skeleton using an intramolecular heck reaction

Masazumi Ikeda; Ken Ichi Hirose; Serry A.A. El Bialy; Tatsunori Sato; Takayuki Yakura; Said M.M. Bayomi

doi:10.1248/cpb.46.1084

Approaches to the cephalotaxine skeleton using an intramolecular heck reaction

Masazumi Ikeda^*, Ken Ichi Hirose, Serry A.A. El Bialy, Tatsunori Sato, Takayuki Yakura, Said M.M. Bayomi

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

24 被引用数 (Scopus)

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1-[2-(o-Iodophenyl)acetyl]-2-(prop-2-enyl)-2-vinylpyrrolidine (17), upon treatment with palladium(II) acetate [Pd(OAc)₂] in the presence of tripheoylphosphine and triethylamine in refluxing acetonitrile, gave the monocylization product 20 as the major product along with a small amount of the tandem cyclization product 21. On the other hand, treatment of the 1-[2- (o-iodophenyl)aeetyl]-1-azaspiro[4.4]non-8-en-7-one (25) with Pd(OAc)₂, 1,3- bis-(diphenylphosphino)propane, tributylphosphine, and silver carbonate in boiling N,N-dimethylformamide afforded the cyclized product 27 in 51% yield.

本文言語	英語
ページ（範囲）	1084-1089
ページ数	6
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	46
号	7
DOI	https://doi.org/10.1248/cpb.46.1084
出版ステータス	出版済み - 1998

ASJC Scopus 主題領域

化学一般
創薬

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10.1248/cpb.46.1084

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@article{a1c33ae44d1140c281571f6fd1a3bffd,

title = "Approaches to the cephalotaxine skeleton using an intramolecular heck reaction",

abstract = "1-[2-(o-Iodophenyl)acetyl]-2-(prop-2-enyl)-2-vinylpyrrolidine (17), upon treatment with palladium(II) acetate [Pd(OAc)2] in the presence of tripheoylphosphine and triethylamine in refluxing acetonitrile, gave the monocylization product 20 as the major product along with a small amount of the tandem cyclization product 21. On the other hand, treatment of the 1-[2- (o-iodophenyl)aeetyl]-1-azaspiro[4.4]non-8-en-7-one (25) with Pd(OAc)2, 1,3- bis-(diphenylphosphino)propane, tributylphosphine, and silver carbonate in boiling N,N-dimethylformamide afforded the cyclized product 27 in 51% yield.",

keywords = "Anti-elimination, Cephalotaxine, Cope rearrangement, Intramolecular Heck reaction, Intramolecular aldol condensation, Tandem Heck reaction",

author = "Masazumi Ikeda and Hirose, {Ken Ichi} and {El Bialy}, {Serry A.A.} and Tatsunori Sato and Takayuki Yakura and Bayomi, {Said M.M.}",

year = "1998",

doi = "10.1248/cpb.46.1084",

language = "英語",

volume = "46",

pages = "1084--1089",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "7",

}

TY - JOUR

T1 - Approaches to the cephalotaxine skeleton using an intramolecular heck reaction

AU - Ikeda, Masazumi

AU - Hirose, Ken Ichi

AU - El Bialy, Serry A.A.

AU - Sato, Tatsunori

AU - Yakura, Takayuki

AU - Bayomi, Said M.M.

PY - 1998

Y1 - 1998

N2 - 1-[2-(o-Iodophenyl)acetyl]-2-(prop-2-enyl)-2-vinylpyrrolidine (17), upon treatment with palladium(II) acetate [Pd(OAc)2] in the presence of tripheoylphosphine and triethylamine in refluxing acetonitrile, gave the monocylization product 20 as the major product along with a small amount of the tandem cyclization product 21. On the other hand, treatment of the 1-[2- (o-iodophenyl)aeetyl]-1-azaspiro[4.4]non-8-en-7-one (25) with Pd(OAc)2, 1,3- bis-(diphenylphosphino)propane, tributylphosphine, and silver carbonate in boiling N,N-dimethylformamide afforded the cyclized product 27 in 51% yield.

AB - 1-[2-(o-Iodophenyl)acetyl]-2-(prop-2-enyl)-2-vinylpyrrolidine (17), upon treatment with palladium(II) acetate [Pd(OAc)2] in the presence of tripheoylphosphine and triethylamine in refluxing acetonitrile, gave the monocylization product 20 as the major product along with a small amount of the tandem cyclization product 21. On the other hand, treatment of the 1-[2- (o-iodophenyl)aeetyl]-1-azaspiro[4.4]non-8-en-7-one (25) with Pd(OAc)2, 1,3- bis-(diphenylphosphino)propane, tributylphosphine, and silver carbonate in boiling N,N-dimethylformamide afforded the cyclized product 27 in 51% yield.

KW - Anti-elimination

KW - Cephalotaxine

KW - Cope rearrangement

KW - Intramolecular Heck reaction

KW - Intramolecular aldol condensation

KW - Tandem Heck reaction

UR - http://www.scopus.com/inward/record.url?scp=0031828105&partnerID=8YFLogxK

U2 - 10.1248/cpb.46.1084

DO - 10.1248/cpb.46.1084

M3 - 学術論文

AN - SCOPUS:0031828105

SN - 0009-2363

VL - 46

SP - 1084

EP - 1089

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 7

ER -

Approaches to the cephalotaxine skeleton using an intramolecular heck reaction

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