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Paper | Regular issue | Vol 34, No. 6, 1992, pp.1147-1167
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6004
■ Stereospecific Synthesis of a Ribosyl-diazepanone Derivatives; a Synthetic Approach for Elucidation of the Stereochemistry of a Lipid Nucleoside Antibiotic Liposidomycin B

Marianne R. Spada, Makoto Ubukata,* and Kiyoshi Isono

*Antibiotics Laboratory, RIKEN(The Institute of Physical and Chemical Research), Wako-shi, Saitama 351-01, Japan

Abstract

A new type of ribosyl-diazepanone derivative (23), the core ribosyl 7-membered heterocycle of the nucleoside antibiotic liposidomycin B has been synthesized using a chiral synthetic route that could offer accessibility to any of possible stereoisomers of 23. Starting from readily available cis-1,4-butenediol and β-D-ribose, epoxides (4) and (14) were obtained. Regioselective nucleophillic ring opening of these epoxides subsequently to the several reaction steps afforded key intermediates amine (9) and azido acid (19) which were ultimately coupled to furnish amide (20). During hydrogenolysis of azido aldehyde (22) an intramolecular Schiff base formation occurred yielding the desired product (23).