Synthesis of d-amicetose and l-rhodinose from l-glutamic acid

✍ Scribed by Giancarlo Berti; Paola Caroti; Giorgio Catelani; Luigi Monti

• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 620 KB
• Volume: 124
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88353-0

✦ Synopsis

L-Glutamic acid has been converted into a separable mixture of D-amicetonoand L-rhodinono-y-lactones by a sequence involving transformation into (S)-y-carboxy-y-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide. Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars. In spite of some improvements in the preparation of 2, the optical yield of this step was only -go%, but one crystallisation from chloroform raised the optical purity to 96%. The subsequent steps produced a loss in optical purity of only 4%.