1-히드록시카르바페넴의 합성에 관한 연구 = Studies on the Synthesis of 1-Hydroxycarbapenems

국문 초록 (Abstract)

4-styryl-2-azetidinone 7b의 bromoacetate에 의한 N-알킬화, 가오존분해, 산화, 말론산 에틸 마그네슘과의 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 oxide와의 1,3 이중극성 고리화 첨가반응, 촉매 수소화 및 디아조화 반응의 일련의 과정을 거쳐서 (3S,4S)-3-[(S)-1-(t-butyldimethylsilyloxy)ethyl]-4-(3-diazo-3-ethoxycarbonyl-1-hydroxypropyl)-2-azetidinone(21)을 합성하였다. 그러나 화합물 14 또는 21을 $Rh_2(OAc)_4$ 로 처리하여 1-hydroxycarbapenem 또는 1-hydroxycarbapenam으로 고리화하는 것을 성공하지 못하였다.

다국어 초록 (Multilingual Abstract)

(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 $Rh_2(OAc)_4$ was unsuccessful.