Novel, stereoselective syntheses of penem antibiotics: efficient, formal syntheses of SCH 34343

Journal Article (Journal Article)

Novel, stereoselective syntheses of (3S, 4R, 5R)-1-(allyloxycarbonyl)methyl-3-[1-hydroxyethyl]-4-β-naphthoxy(thi ocarbonyl)thio-2-azetidinone (13) and (3S, 4R, 5R, 3′S, 4′R, 5′R)-4,4′-dithio-bis-1-(allyloxy-carbonyl)methyl-3-[-1-hydro xyethyl]-2-azetidinone (22), key intermediates in the synthesis of the penem antibiotic Sch 34343, were developed starting from readily available 6-aminopenicillanic acid. Advantages of these routes include 1) the highly stereospecific introduction of the hydroxyethyl sidechain with the desired (R)-configuration and 2) the retention of the sulfur of the starting material. © 1993.

Full Text

Duke Authors

Cited Authors

  • Hou, D; Mas, JL; Chan, TM; Wong, YS; Steinman, M; McPhail, AT

Published Date

  • January 1, 1993

Published In

Volume / Issue

  • 3 / 11

Start / End Page

  • 2171 - 2176

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/S0960-894X(01)80920-3

Citation Source

  • Scopus