A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction

Sung Ho Kang; Mihyong Kim; Do Hyun Ryu

doi:10.1055/s-2003-39910

A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction

Sung Ho Kang, Mihyong Kim, Do Hyun Ryu

Korea Advanced Institute of Science and Technology

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

11 Scopus citations

Abstract

A stereocontrolled synthesis of azetidinone 3 as a key intermediate to 1β-methylcarbapenem 2 has been achieved via iodoamidation of trichloroacetimidate prepared from (Z)-olefinic allylic alcohol 6, aziridine ring-opening reaction with cyanide nucleophile and a tandem β-lactam formation.

Original language	English
Pages (from-to)	1149-1150
Number of pages	2
Journal	Synlett
Issue number	8
DOIs	https://doi.org/10.1055/s-2003-39910
State	Published - 2003
Externally published	Yes

Keywords

1β-methylcarbapenem
Aziridine ring-opening
Iodoamidation
Stereoselective synthesis
Tandem β-lactam formation

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10.1055/s-2003-39910

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title = "A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction",

abstract = "A stereocontrolled synthesis of azetidinone 3 as a key intermediate to 1β-methylcarbapenem 2 has been achieved via iodoamidation of trichloroacetimidate prepared from (Z)-olefinic allylic alcohol 6, aziridine ring-opening reaction with cyanide nucleophile and a tandem β-lactam formation.",

keywords = "1β-methylcarbapenem, Aziridine ring-opening, Iodoamidation, Stereoselective synthesis, Tandem β-lactam formation",

author = "Kang, \{Sung Ho\} and Mihyong Kim and Ryu, \{Do Hyun\}",

year = "2003",

doi = "10.1055/s-2003-39910",

language = "English",

pages = "1149--1150",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction

AU - Kang, Sung Ho

AU - Kim, Mihyong

AU - Ryu, Do Hyun

PY - 2003

Y1 - 2003

N2 - A stereocontrolled synthesis of azetidinone 3 as a key intermediate to 1β-methylcarbapenem 2 has been achieved via iodoamidation of trichloroacetimidate prepared from (Z)-olefinic allylic alcohol 6, aziridine ring-opening reaction with cyanide nucleophile and a tandem β-lactam formation.

AB - A stereocontrolled synthesis of azetidinone 3 as a key intermediate to 1β-methylcarbapenem 2 has been achieved via iodoamidation of trichloroacetimidate prepared from (Z)-olefinic allylic alcohol 6, aziridine ring-opening reaction with cyanide nucleophile and a tandem β-lactam formation.

KW - 1β-methylcarbapenem

KW - Aziridine ring-opening

KW - Iodoamidation

KW - Stereoselective synthesis

KW - Tandem β-lactam formation

UR - https://www.scopus.com/pages/publications/0037715351

U2 - 10.1055/s-2003-39910

DO - 10.1055/s-2003-39910

M3 - Article

AN - SCOPUS:0037715351

SN - 0936-5214

SP - 1149

EP - 1150

JO - Synlett

JF - Synlett

IS - 8

ER -

A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction

Abstract

Keywords

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