Palladium-catalyzed intramolecular addition of trisilanes to carbon-carbon double bonds. Polyol synthesis by use of a disilanyl group as a hydroxyl equivalent

✍ Scribed by Michinori Suginome; Shin-ichiro Matsunaga; Taisuke Iwanami; Akira Matsumoto; Yoshihiko Ito

• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 261 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02075-8

✦ Synopsis

Intramolecular cyclization

of trisilanyl ethers of homoallylalcohols proceeded regio-and stereoselectively with a 5-exo mode to give 3-(disilanylmethyl)-24latetrahydrofuran derivatives in good yields in the presence of a t-alkyl isonitrile-palladium catalyst. From the cyclized products thus obtained were synthesized polyols including the key intermediate in the total synthesis of (-)avenaciolide via stepwise oxidation of the silyl and disilanyl groups.