3457identical with those of samples obtained from the cryptand and alkaline iodide. Their purity (95-100%) was also tested by potentiometric titration of iodide ion. [2.2.2,CI4] was isolated as the free cryptand after decomplexation in an acidic medium and the addition of LiOH (entry 13).
Registry No. 2 (x= OMes), 80322-79-8; 3 (X = I), 92958-34-4; 3 (free base), (K complex), 97485-94-4; 26 (Na complex), 97485-95-5; 27, 64066-13-3; CH,-(CH2)&H(CO2H)OCH2CH20H, 97431-36-2; diglycolic acid dichloride, 21062-20-4; 2-bromopalmitoyl chloride, 69319-95-5; 2-(benzyloxy)ethanol, 622-082; methanesulfonyl chloride, 124-63-0; 1,5-dichloro-3-oxapentane, 111-44-4. Clavalanine (Ro 22-5417), a New Clavam Antibiotic from Streptomyces clavuligerus . 4. Clavalanine (Ro 22-5417), a new p-lactam antibiotic, 3-[(3S,5S)-7-oxo-l-aza-4oxabicyclo[3.2.0]hept-3-yl]-~-alanine (l), was synthesized by a route in which D-XylOSe (4) supplied the stereochemical requirements. From 4 was elaborated a (25',4S)-2-amin0-4,5-dihydroxypentanoic acid derivative (16), which was condensed with 4-acetoxy-2-azetidinone (3) to afford with good diastereoselectivity, after final removal of protecting groups, the desired clavam 1. (1) Reading, C; Cole, M. Antimicrob. Agents Chemother. 1977,11,852 (2) Pruess, D. L.; Kellett, M. J. Antibiot. 1983, 36, 208. (3) Evans, R. H.; Ax, H.; Jacoby, A.; Williams, T. H.; Jenkins, E.; (4) Muller, J . C.; Toome, V.; Pruess, D. L.; Blount, J. F.; Weigele, M. and references therein. Scannell, J . J. Antibiot. 1983, 36, 213. J . Antibiot. 1983, 36, 217.
