C-C bond formation on reduction of organomercurial and its application to biomimetic synthesis of strobane carbon skeleton

✍ Scribed by Yasuo Matsuki; Mitsuaki Kodama; Shô Itô

• Book ID: 104237900
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 200 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86509-6

✦ Synopsis

The bicyclic ethers obtained by the oxymercuration-demercuration reaction of linalool was found to be formed in the demercurotion step. The facile C-C bond formation is due to the proximity of Hg and the vinyl group in the organomercurial intermediate. Applying this process to epimanool a biomimetic synthesis of strobane carbon skeleton was achieved.