Synthesis of ribosylhopane, the putative biosynthetic precursor of bacterial triterpenoids of the hopane series

✍ Scribed by Tore Duvold; Michel Rohmer

• Book ID: 104209545
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 801 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00567-0

✦ Synopsis

AbstracL A versatile, efficient route to ribosylhopane with control over all asymmetric carbon atoms of the side-chain is presented. The synthesis is based on two chain elongations starting from diploptene by subsequent additions of two acetylenic moieties. In a key step a keto-propiolate is stereoselectively reduced to the corresponding hydroxy-propiolate by means of a chiral oxazaborolidine assisted hydroboration. This synthetic protocol represents a useful tool for the access to natural and unnatural bacteriohopanepolyol derivatives of biological interest as well as to labeled ribosylhopane and bacteriohopanetetrol for biosynthetic studies.