Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction

Takuzo Komiyama; Yutaka Takaguchi; Sadao Tsuboi

doi:10.3987/COM-05-S(K)57

Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction

Takuzo Komiyama, Yutaka Takaguchi, Sadao Tsuboi

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

3 Citations (Scopus)

Abstract

A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.

Original language	English
Pages (from-to)	147-151
Number of pages	5
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(K)57
Publication status	Published - Dec 31 2005

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-05-S(K)57

Fingerprint Dive into the research topics of 'Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction'. Together they form a unique fingerprint.

Cite this

@article{18d244e645554375b91a6f281c125b4e,

title = "Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction",

abstract = "A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.",

author = "Takuzo Komiyama and Yutaka Takaguchi and Sadao Tsuboi",

year = "2005",

month = dec,

day = "31",

doi = "10.3987/COM-05-S(K)57",

language = "English",

volume = "66",

pages = "147--151",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

TY - JOUR

T1 - Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction

AU - Komiyama, Takuzo

AU - Takaguchi, Yutaka

AU - Tsuboi, Sadao

PY - 2005/12/31

Y1 - 2005/12/31

N2 - A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.

AB - A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.

UR - http://www.scopus.com/inward/record.url?scp=33646875725&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646875725&partnerID=8YFLogxK

U2 - 10.3987/COM-05-S(K)57

DO - 10.3987/COM-05-S(K)57

M3 - Article

AN - SCOPUS:33646875725

VL - 66

SP - 147

EP - 151

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 1

ER -