Synthesis of chiral 1,2-diols and related compounds of biological activities via stepwise ring fission of 5-alkyl-6,8-dioxabicyclo[3.2.1]octane skeleton

✍ Scribed by Yukio Masaki; Yuzuru Serizawa; Kinnosuke Nagata; Hirohisa Oda; Hiromu Nagashima; Kenji Kaji

• Book ID: 104218098
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 264 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)83984-2

✦ Synopsis

octanes, prepared from (+)-tartaric acid, were converted by means of an organoaluminium reagent Et2AlSPh into the pyranoid monothioacetals, which were utilized via the successive thioacetalization to the synthesis of the insect pheromones (+)-disparlure and (-)-(2S,3S)-octanediol.