Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex

✍ Scribed by Hiroaki Yuasa; Gouki Makado; Yoshiyasu Fukuyama

• Book ID: 104254151
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 159 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01537-5

✦ Synopsis

The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a p-allylpalladium complex and a b-ketoester nucleophile. Subsequent reduction of epoxide in 1a with LiAlH 4 gave a diol, which was identical with that derived from vibsanin F.