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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 42, Number 1
JKCSEZ 42(1)
February 20, 1998 

 
Title
Studies on the Synthesis of 1-Hydroxycarbapenems

1-히드록시카르바페넴의 합성에 관한 연구
Author
Jong hyeon You, Jeong-Ho Park, Yang Mo Goo, Youn Young Lee*

유종현, 박정호, 구양모, 이윤영
Keywords
Abstract
4-styryl-2-azetidinone 7b의 bromoacetate에 의한 N-알킬화, 가오존분해, 산화, 말론산 에틸 마그넴슘과의 축합 및 디아조 전달반응의 일련의 과정을 거처서 (3S,4S)-1-(t-Butoxycarbonylmethyl)-3-[(S)-1-(t-butyldimethylsilyloxy)ethyl]-4-(2-diazo-2-ethoxycarbonyl-1-oxoethyl)-2-azetidinone(14)을 합성하였다. 또한 4-formyl-2-azetidinone 5b 의 Wittig 반응, ethoxycarbonylformonitrile oxide 와의 1,3 이중극성 고리화 텀가반응, 촉매 수소와ㅏ 및 디아조화 반응의 일련의 과정을 거쳐서 (3S,4S)-3-[(S)-1-(t-Butyldimethylsilyloxy)ethyl]-4-(3-diazo-3-ethoxycarbonyl1-hydroxypropyl)-2-azetidinone (21)을 합성하였다. 그러나 화합물 14 또는 21을 Rh2(OAc)4 로 처리하여 hydroxycarbapenem 또는1-hydroxycarbapenam 으로 고리화 하는 것을 성공하지 못했다.

(3S,4S)-1-(t-Butoxycarbonylmethyl)-3-[(S)-1-(t-butyldimethylsilyloxy)ethyl]-4-(2-diazo-2-ethoxycarbonyl-1-oxoethyl)-2-azetidinone (14) was prepared from 4-styryl-2-azetidinone 7b via a sequence of reactions involving N-alkylation with bromoacetate, ozonolysis, oxidation, condensation with magnesium ethyl malonate, and diazo transfer reaction. (3S,4S)-3-[(S)-1-(t-Butyldimethylsilyloxy)ethyl]-4-(3-diazo-3-ethoxycarbonyl1-hydroxypropyl)-2-azetidinone (21) was also prepared from 4-formyl-2-azetidinone 5b via a sequence of reactions involving Wittig reaction, 1,3-dipolar cycloaddition with ethoxycarbonylformonitrile oxide, catalytic hydrogenation, and diazotization. However, the final cyclization of 14 or 21 to 1-hydroxycarbapenem or 1-hydroxycarbapenam by treating with Rh2(OAc)4 was unsuccessful.K980012

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