Simple, stereocontrolled synthesis of 1β-methylcarbapenem antibiotics from 3()-hydroxybutyric acid
1986; Elsevier BV; Volume: 27; Issue: 19 Linguagem: Inglês
10.1016/s0040-4039(00)84472-x
ISSN1873-3581
AutoresTakamasa Iimori, Masakatsu Shibasaki,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA simple, stereocontrolled synthesis of 1β-methylcarbapenem antibiotics has been accomplished. The synthesis involves stereoselective aldol-type condensation of vinyloxyborane derived from S-phenyl 3(R)-hydroxybutanethioate with N-3-trimethylsilyl-2-propynylidenebenzylamine, regiocontrolled hydroesterification of terminal acetylene and stereoselective 1,4-reduction of the α,β-unsaturated ester as key steps.
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