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Communication | Regular issue | Vol 27, No. 9, 1988, pp.2107-2110
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4690
Kinetic Resolution of 2-Furylcarbinols Using the Sharpless Oxidation and Its Application to the Synthesis of (5R,6S)-6-Acetoxy-5-hexadecanolide

Tetsuji Kametani,* Masayoshi Tsubuki, Yoko Tatsuzaki, and Toshio Honda

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Kinetic resolution of 2-furylcarbinols employing 10 mol % of Ti(0iPr)4 in the presence of molecular sieves 3A under the Sharpless oxidation condition generally affords corresponding optically actlve 2-furylcarbinols in a range of 80-98% ee. Application of the optically active 1f to the synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide (8), the major component of the oviposition attractant pheromone of the mosquito Culex pipens fatigans, has also been achieved.