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Communication | Special issue | Vol 54, No. 2, 2001, pp.585-588
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)76
Diastereocontrol in the Reaction of (R)- 2,2-Dimethyl-4-acyl-1,3-dioxolanes with Alkylmetals: A Facile Entry to Enantiopure Terpenetriols

Hisashi Mikoshiba, Koichi Mikami, and Takeshi Nakai*

*Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan


The reactions of the 4-acetyldioxolane with terpenoid Grignard reagents are shown to proceed predominantly through the α-chelation model to give the syn-triol derivatives in ~70% selectivity. A novel and efficient protocol to effect the stereoselective methylation onto the terpenoid-derived 4-acyldioxolanes has been developed which affords the desired anti-terpenetriols in high stereopurities.