✦ LIBER ✦

Nuclear analogs of .beta.-lactam antibiotics. 6. 3-Oxa-1-azabicyclo[4.2.0]octan-8-one-2-carboxylic acids

✍ Scribed by Gleason, John G.; Buckley, T. F.; Holden, Kenneth G.; Bryan, D. Boles; Siler, P.

Book ID: 120645729
Publisher: American Chemical Society
Year: 1979
Tongue: English
Weight: 335 KB
Volume: 101
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00510a050

No coin nor oath required. For personal study only.

📜 SIMILAR VOLUMES

Nuclear analogs of .beta.-lactam antibio

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

✍ Bryan, D. Boles; Hall, Ralph F.; Holden, Kenneth G.; Huffman, William F.; Gleaso 📂 Article 📅 1977 🏛 American Chemical Society 🌐 English ⚖ 359 KB

Synthetic carbapenem antibiotics II. Ste

Synthetic carbapenem antibiotics II. Stereoisomers of 7-hydroxyethyl-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.O]octan-8-one

✍ David H. Shih; Judith A. Fayter; L.D. Cama; Burton G. Christensen; Jordan Hirshf 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 243 KB

The titled compounds are key synthetic intermediates in the structure-activity relationship studies of novel l-methyl carbapenem antibiotics. Preparation and structural determination of these stereoisomers by X-ray crystallography and proton NMR spectroscopy are reported.

Nuclear analogs of .beta.-lactam antibio

Nuclear analogs of .beta.-lactam antibiotics. 1. The total synthesis of a 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid via a versatile monocyclic .beta.-lactam intermediate

✍ Huffman, William F.; Holden, Kenneth G.; Buckley, Thomas F.; Gleason, John G.; W 📂 Article 📅 1977 🏛 American Chemical Society 🌐 English ⚖ 239 KB

Free-radical annelation in the synthesis

Free-radical annelation in the synthesis of bicyclic β-lactams. 1. Synthesis of 8-oxo-5-oxa-1-azabicyclo[4.2.0]octane and 9-oxo-6-oxa-1-azabicyclo[5.2.0]nonane derivatives

✍ Mario D. Bachi; Christian Hoornaert 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 199 KB

A new method for the synthesis of some fused bicyclic B-lactams based on the completion of the molecular backbone by a free-radical C-C bond forming reaction is described. Many of the synthetic approaches to the fused bicyclic molecular backbone of B-lactam antibiotics are based on the annelation of

Synthesis of ethyl cis 2-[(Diethoxyphosp

Synthesis of ethyl cis 2-[(Diethoxyphosphoryl)methyl]-7-oxo-3-phenyl-6-phthalimido-l-azabicyclo[3.2.0]hept-3-ene-2-carboxylate and Methyl cis-2-Bromo-3-methyl-8-oxo-7-phthalimido-4-oxa-1-azabicyclo[4.2.0]octane-2-carboxylate

✍ Gholam H. Hakimelahi; Ali A. Jarrahpour 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 German ⚖ 384 KB

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

Reactions of 4-Oxoalkanoic Acids, 4. Syn

Reactions of 4-Oxoalkanoic Acids, 4. Synthesis of (±)-6-Alkyl-5-oxa-1-azabicyclo[4.3.0]nonan-9-ones, (±)-5-Alkyl-4-oxa-1-azabicyclo[3.3.0]octan-8-ones, and Substituted 1,6-Dioxa-3,8-diazacyclodecanes by Reaction of Ethyl 4-Oxoalkanoates with 3-Aminopropanol and 2-Aminoethanol

✍ Wedler, Christine ;Schick, Hans ;Scharfenberg-Pfeiffer, Doris ;Reck, Günter 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 432 KB

## Abstract Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Å in almost quantitative yield with 3‐aminopropanol and 2‐aminoethanol to form the bicyclic lactams __rac__‐2 and __rac__‐3, respectively. Surprisingly, the (±)‐5‐alkyl‐4‐oxa‐1‐azab