Deoxy-nitrosugars, 7th communication Synthesis of methyl shikimate and of diethyl phosphashikimate from D-ribose

✍ Scribed by Sohail Mirza; Andrea Vasella

• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: German
• Weight: 424 KB
• Volume: 67
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19840670621

✦ Synopsis

Abstract

The chain elongation of the deoxy‐nitroribose 6 by a Michael addition to the vinyl‐phosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87%). From 11, the key intermediates 15 and 16 (77%) were obtained by a highly diastereoselective reduction, followed by detritylation, periodate cleavage, and silylation. Methoxycarbonylation of 15 and 16 gave 17 and 18 which were converted into methyl shikimate (21; 79%) by intramolecular olefination and partial deprotection. Similarly, phosphonoylation of 16 gave 22 (99%) which was transformed into the diethyl phosphashikimate 2 (53% from 6).