𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A new total synthesis of (±)-clavulanic acid

✍ Scribed by Peter H. Bentley; Gerald Brooks; Martin L. Gilpin; Eric Hunt

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
128 KB
Volume
20
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Regioselective reactions at the terminal double bond of the racemic azetidinone dienylether (4), provides a source of clavulanic acid and several analogues.

We have recently reported la the first total synthesis of (t)-olavulenic acid (l), which relied upon the construction, double-bond isomerisation and selective ester reduction of the diester (3). We now describe an alternative synthesis, which proceeds via the diene (4).

Unlike (3), this diene has the same geometry about the exocyclic double-bona as (1) and we

📜 SIMILAR VOLUMES

New reactions in clavulanic acid biosynt
New reactions in clavulanic acid biosynthesis
✍ Craig A Townsend 📂 Article 📅 2002 🏛 Elsevier Science 🌐 English ⚖ 160 KB

Clavulanic acid is only a modestly effective antibiotic against bacterial infections in humans, but a potent inhibitor/inactivator of beta-lactamase enzymes that confer bacterial resistance. The biosynthetic pathway to clavulanic acid is considerably more complex than that to the structurally relate

Total synthesis of thienamycin: a new ap
Total synthesis of thienamycin: a new approach from aspartic acid
✍ Paul J. Reider; Edward J.J. Grabowski 📂 Article 📅 1982 🏛 Elsevier Science 🌐 French ⚖ 176 KB

Recently, Salzmann et al.' have reported a synthesis of thienamycin (1) in which the chirality at C5 was derived from L-aspartic acid (I\_).