Concepedia

A Facile Access to 3-Hydroxycephems from Penicillin G through Bi/Sn or Ti/Sn Redox-Promoted Cyclization of 4-(Phenylsulfonylthio)azetidinones

Hideo Tanaka, Masatoshi Taniguchi, Yutaka Kameyama, Marc Monnin, Michio Sasaoka, Takashi Shiroi, Shigemitsu Nagao, Sigeru Torii

Chemistry Letters · 1990 · 11 citations · 11 references

DOI

Concepts

Abstract

Abstract Direct conversion of 1-(3-chloro-2-hydroxy-1-p-methoxybenzyloxycarbonyl-1-propenyl)-4-(phenylsulfonylthio)azetidinones derived from penicillin G into 3-hydroxycephems was performed successfully by the action with BiCl4/Sn or TiCl4/Sn bimetal redox couples in DMF containing pyridine.

References

11

Neue β‐Lactam‐Antibiotika. Über Derivate der 3‐Hydroxy‐7‐amino‐ceph‐3‐em‐4‐carbonsäure. Modifikationen von Antibiotika, 10. Mitteilung [1]

Riccardo Scartazzini, H. Bickel · Helvetica Chimica Acta · 1974 · 40 citations

, , +10

A general route to 3-functionalized 3-norcephalosporins

Vittorio Farina, Stephen Baker, Sheila I. Hauck · The Journal of Organic Chemistry · 1989 · 37 citations

, , +5

Chemistry of cephalosporin antibiotics. XXIX. 3-Halo- and 3-methoxy-3-cephems

Robert R. Chauvette, Pamela A. Pennington · Journal of the American Chemical Society · 1974 · 32 citations

, , +7

Penicillin-cephalosporin conversion III. A Novel route to 3-chloromethyl-Δ3-cephems

Sigeru Torii, Hideo Tanaka, Norio Saitoh et al. · Tetrahedron Letters · 1982 · 26 citations

, , +2

Synthetic studies related to oral β-lactam antibiotics

M. YOSHIOKA · Pure and Applied Chemistry · 1987 · 21 citations · Full text

, , +7