Nuclear analogs of .beta.-lactam antibiotics. 2. The total synthesis of 8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids
โ Scribed by Bryan, D. Boles; Hall, Ralph F.; Holden, Kenneth G.; Huffman, William F.; Gleason, John G.
- Book ID
- 111859922
- Publisher
- American Chemical Society
- Year
- 1977
- Tongue
- English
- Weight
- 359 KB
- Volume
- 99
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
Allylic oxidation of 4-allyl-1-dimethyl-t-butylsilylazetidin-2ones (5,7) gave the 4-(l-hydroxyprop-2-ene-1-yl) derivatives (6,8). Radical benzoyloxylation of the silylated 8-oxo-7-azabicyclo[4.2.O]oct-3ene (18) provided four allylic monobenzoates. Progression of ( ) and ( ) afforded, respectively,
3R)-4-Acetoxy-3-trimethylsilyl-2-azetidinone, was converted into optically pure benzyl penicillanate in seven steps (22%) using (benzyloxy)nitromethane as a reagent for ring annulation.
The synthesis of a d'carbapenem and two ,?-lactams possessing a Br-atom at the N-substituting center not involved in the lactam ring and bearing the carboxyl group is described. The ,?-lactams having this kind of Br-substitution are more susceptible to nucleophilic attack than those having a conjuga