Journal of the Chemical Society. Perkin transactions I p. 2851 - 2856 (1996)
Update date:2022-08-05
Topics:
Seki, Masahiko
Kondo, Kazuhiko
Iwasaki, Tameo
A seven-step efficient synthesis of 1β-methylcarbapenems 1 from the acetoxyazetidinone 6 is described. The Reformatsky reaction of 3-(2-bromopropionyl)-1,3-benzoxazinone 7 with compound 6 gave an adduct 8 in 96% yield with high β-selectivity (β:α = 92:8). Compound 8 was transformed in three steps into the side-chain thiol esters 12a-e in good yields. The chlorotrimethylsilane-mediated Dieckmann-type cyclisation of thioesters 12b-e followed by counter-attack of the liberated thiolate anion 18 yielded the C-2 alkylthio- or arylthio-substituted 1β-methylcarbapenems 19b-e in a one-pot procedure. The synthesis of 1β-methylcarbapenems 1 was demonstrated by a simple cleavage of the silyl ether and allyl ester of compound 19b to afford target compound 1b in high yield.
View MoreBeijing Wisdom Chemicals Co., Ltd.
Contact:+86-10-52350335
Address:F2, BLDG 19, Liando Valley U, Majuqiao, Tongzhou District, Beijing, China
Changzhou Xuanming Chemical Co., Ltd.
Contact:86 0519 85525329
Address:China Town, Xinbei, Changzhou, Jiangsu Room 6019
Contact:+86-25-52346955
Address:199,JIANYE ROAD,NANJING,CHINA
Winchem Industrial Co. Ltd.(expird)
Contact:86-574-83851061 86-574-87083208
Address:Room 905, No.3 Building,East Business Center, 456 Xingning Road, Ningbo City,China
Shanghai Standard Biotech Co., Ltd.
Contact:+86-18502101150
Address:Room 103, Building 2nd, NO.720, Cailun Road , Pudong District, Shanghai, China
Doi:10.1016/0040-4039(95)00543-L
(1995)Doi:10.1021/jo962180u
(1997)Doi:10.1002/anie.202109089
(2021)Doi:10.1016/j.jfluchem.2014.06.011
(2014)Doi:10.1246/bcsj.54.1821
(1981)Doi:10.1016/j.jorganchem.2008.09.054
(2009)
