Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under Mitsunobu conditions

✍ Scribed by Isidro G. Collado; James R. Hanson; Rosario Hernández-Galán; Peter B. Hitchcock; Antonio J. Macías-Sánchez; Juan C. Racero

• Book ID: 104262118
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 131 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01335-0

✦ Synopsis

Treatment of 8-methoxy-isocaryolan-9cx-ol (!) with acid on the one hand and with diethyl azedicarboxylate (DEAD)/triphenylphosphine on the other, leads to different pinacol rearrangements of the isacaryolane skeleton. IS,2S,5R, 9R-8-oxo-l,4,4-U'imethyltricyclo[7.2.1.O~5]dodecane (2), which possesses a novel sesquiterpenoid skeleton, was obtained under Mitsunobu conditions.