Chemistry of O-Silylated Ketene Acetals : A Stereoselective Synthesis of Optically Active Carbapenem Antibiotics, (+)-Thienamycin and (+)-PS-5

A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Michael addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for(+)-PS-5 was also prepared from 4-(phenylsulfinylmethyl)butanamide (21).

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 40; no. 1; pp. 12 - 20
Main Authors KITA, Yasuyuki, SHIBATA, Norio, MIKI, Takashi, TAKEMURA, Yumiko, TAMURA, Osamu
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 01.01.1992
Maruzen
Subjects
(+)-PS-5
(+)-thienamycin
carbapenem antibiotics
Chemistry
diastereoselective Michael addition
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
O-silylated ketene acetal
Organic chemistry
Preparations and properties
silicon-induced Pummerer-type reaction
synthesis
Michael addition
Stereoselectivity
Four membered ring
Nitrogen heterocycle
Pummerer reaction
Lactam
Chiral compound
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Summary:A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Michael addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for(+)-PS-5 was also prepared from 4-(phenylsulfinylmethyl)butanamide (21).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.40.12