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Efficient and practical synthesis of 1⊝methylcarbapenems

✍ Scribed by Masaharu Kume; Hiroaki Ooka; Hiroyuki Ishitobi

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
794 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

An efficient and practical method of synthesizing lP-methylcarbapenem, S-4661, was developed.

(4R)-4-I (IS)-1-Methylallyl]-2.azetidinone 2, prepared stereoselectively from commercially available acetoxy-azetidinone 3, was converted to the P-keto ester6 in four steps. The iodonium ylide 5 was prepared from 6, then cyclized to obtain the bicyclic P-keto ester 4. Finally. 4 was processed to the target product, S-4661, by conventional procedures.

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Rcclction of acctoxy-xxctidinone 4, (Z)-crotylbromidc 5 xnd Zn sclcctively gave 6. which was eollvcrtcd to @-~Yl-2-chYdroXY-ttYl~ 11,8kcyiatcmlcdiateinayllW&30f xntibia6c2,inlQbovcrxllyield. 2-Functionalized-methyl-1 ~methylcarbapenem antibiotics 1 1.2, which can be clearly distinguished from conven