Simple, stereocontrolled synthesis of 1β-methylcarbapenem antibiotics from 3(R)-hydroxybutyric acid
✍ Scribed by Takamasa Iimori; Masakatsu Shibasaki
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 292 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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## Abstract Racemic, R‐ and S‐β‐hydroxybutyric acid were labelled with ^11^C in the carboxylic position by a two‐step stereospecific synthesis starting with carrier‐added [^11^C]cyanide and R/S, R‐ or S‐propylene oxide. Hydrolysis of the intermediate nitrile with hydrochloric acid gave racemic [1‐^
Alcohols 4\_ and s prepared from 3 underwent completely stereospecific etherification to give l-oxacephams 2 and s which were converted into the 1-oxacephem nucleus 2 via kaand lc. Functionalization at C-3' in 6 and &was unsuccessful. Since 7a-methoxy-1-oxacephem & (6059-S) was found to be a highly