Synthesis of octahydrobenzo[b]furans using tandem conjugate addition reactions initiated by oxygen nucleophile

Takayuki Yakura; Seiji Yamada; Mari Shima; Masae Iwamoto; Masazumi Ikeda

doi:10.1248/cpb.46.744

Synthesis of octahydrobenzo[b]furans using tandem conjugate addition reactions initiated by oxygen nucleophile

Takayuki Yakura, Seiji Yamada, Mari Shima, Masae Iwamoto, Masazumi Ikeda^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

When 1-nitrocyclohexene (1) was treated with methyl 4-hydroxy-2- butynoate (2) in the presence of potassium tert-butoxide in tetrahydrofuran- tert-butanol at 0°C for 10 min, a tandem conjugate addition product, methyl cis-3a-nitrooctahydrobenzo[b]furan-Δ(3.α)-acetate (3a), was obtained in quantitative yield as a 55:45 mixture of the (Z)- and (E)-isomers. The scope and limitations of this reaction were examined. Some transformation reactions of 3a are also described.

Original language	English
Pages (from-to)	744-748
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	46
Issue number	5
DOIs	https://doi.org/10.1248/cpb.46.744
State	Published - 1998

Keywords

1- Nitrocyclohexene
Methyl 4-hydroxy-2-butynoate
Octahydrobenzo[b]furan
Tandem conjugate addition reaction
X-ray analysis

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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10.1248/cpb.46.744

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title = "Synthesis of octahydrobenzo[b]furans using tandem conjugate addition reactions initiated by oxygen nucleophile",

abstract = "When 1-nitrocyclohexene (1) was treated with methyl 4-hydroxy-2- butynoate (2) in the presence of potassium tert-butoxide in tetrahydrofuran- tert-butanol at 0°C for 10 min, a tandem conjugate addition product, methyl cis-3a-nitrooctahydrobenzo[b]furan-Δ(3.α)-acetate (3a), was obtained in quantitative yield as a 55:45 mixture of the (Z)- and (E)-isomers. The scope and limitations of this reaction were examined. Some transformation reactions of 3a are also described.",

keywords = "1- Nitrocyclohexene, Methyl 4-hydroxy-2-butynoate, Octahydrobenzo[b]furan, Tandem conjugate addition reaction, X-ray analysis",

author = "Takayuki Yakura and Seiji Yamada and Mari Shima and Masae Iwamoto and Masazumi Ikeda",

year = "1998",

doi = "10.1248/cpb.46.744",

language = "英語",

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pages = "744--748",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

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T1 - Synthesis of octahydrobenzo[b]furans using tandem conjugate addition reactions initiated by oxygen nucleophile

AU - Yakura, Takayuki

AU - Yamada, Seiji

AU - Shima, Mari

AU - Iwamoto, Masae

AU - Ikeda, Masazumi

PY - 1998

Y1 - 1998

N2 - When 1-nitrocyclohexene (1) was treated with methyl 4-hydroxy-2- butynoate (2) in the presence of potassium tert-butoxide in tetrahydrofuran- tert-butanol at 0°C for 10 min, a tandem conjugate addition product, methyl cis-3a-nitrooctahydrobenzo[b]furan-Δ(3.α)-acetate (3a), was obtained in quantitative yield as a 55:45 mixture of the (Z)- and (E)-isomers. The scope and limitations of this reaction were examined. Some transformation reactions of 3a are also described.

AB - When 1-nitrocyclohexene (1) was treated with methyl 4-hydroxy-2- butynoate (2) in the presence of potassium tert-butoxide in tetrahydrofuran- tert-butanol at 0°C for 10 min, a tandem conjugate addition product, methyl cis-3a-nitrooctahydrobenzo[b]furan-Δ(3.α)-acetate (3a), was obtained in quantitative yield as a 55:45 mixture of the (Z)- and (E)-isomers. The scope and limitations of this reaction were examined. Some transformation reactions of 3a are also described.

KW - 1- Nitrocyclohexene

KW - Methyl 4-hydroxy-2-butynoate

KW - Octahydrobenzo[b]furan

KW - Tandem conjugate addition reaction

KW - X-ray analysis

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U2 - 10.1248/cpb.46.744

DO - 10.1248/cpb.46.744

M3 - 学術論文

AN - SCOPUS:0031805675

SN - 0009-2363

VL - 46

SP - 744

EP - 748

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 5

ER -

Synthesis of octahydrobenzo[b]furans using tandem conjugate addition reactions initiated by oxygen nucleophile

Abstract

Keywords

ASJC Scopus subject areas

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