In a previous communication' we described base-catalyzed rearrangement of the imino chloride 1 of penicillin V methyl ester to oxazole 9. In the work described herein we report formation of novel B-lactam 8 which arises, after a complicated series of steps, from the interaction of 1 with ketene 3.
Lactams. X. Total synthesis of 5,6-trans-penicillin V methyl ester
โ Scribed by Bose, Ajay K.; Spiegelman, G.; Manhas, M. S.
- Book ID
- 125330674
- Publisher
- American Chemical Society
- Year
- 1968
- Tongue
- English
- Weight
- 399 KB
- Volume
- 90
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2cL methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF2a, an useful tool for biological s
Total Synthesis of 15(RS)-5,6-Dehydro-8-epi-PGF2ฮฑ Methyl Ester by a Biomimetic Process. -Using diacetone D-glucose (I) as starting material the first total synthesis of the title compound (IV) is achieved. Key step is a final biomimetic 5-exo-radical cyclization of the highly functionalized precurs