Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives

Ohi Hidenori; Susumu Inoue; Yoshiharu Iwabuchi; Hiroshi Irie; Susumi Hatakeyama

Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives

Ohi Hidenori, Susumu Inoue, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

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

Abstract

Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.

Original language	English
Pages (from-to)	1757-1759
Number of pages	3
Journal	Synlett
Issue number	11
Publication status	Published - 1999 Jan 1
Externally published	Yes

Keywords

Acyloxonium ion
Eight-membered lactones
Octalactin analogs
Ring enlargement
Silicon compounds

ASJC Scopus subject areas

Organic Chemistry

Cite this

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title = "Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives",

abstract = "Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.",

keywords = "Acyloxonium ion, Eight-membered lactones, Octalactin analogs, Ring enlargement, Silicon compounds",

author = "Ohi Hidenori and Susumu Inoue and Yoshiharu Iwabuchi and Hiroshi Irie and Susumi Hatakeyama",

year = "1999",

month = jan,

day = "1",

language = "English",

pages = "1757--1759",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

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TY - JOUR

T1 - Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives

AU - Hidenori, Ohi

AU - Inoue, Susumu

AU - Iwabuchi, Yoshiharu

AU - Irie, Hiroshi

AU - Hatakeyama, Susumi

PY - 1999/1/1

Y1 - 1999/1/1

N2 - Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.

AB - Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.

KW - Acyloxonium ion

KW - Eight-membered lactones

KW - Octalactin analogs

KW - Ring enlargement

KW - Silicon compounds

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UR - http://www.scopus.com/inward/citedby.url?scp=0344672450&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0344672450

SP - 1757

EP - 1759

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 11

ER -

Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives

Abstract

Keywords

ASJC Scopus subject areas

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