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Communication | Special issue | Vol 52, No. 2, 2000, pp.525-528
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S60
Enantioselective Synthesis of (+)-Decarestrictine L from (2E,5E)-Dibenzyloxy-2,5-heptadien-4-ol

Tomoyuki Esumi, Rieko Kimura, Masako Mori, Yoshiharu Iwabuchi, Hiroshi Irie, and Susumi Hatakeyama*

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


(+)-Decarestrictine L has been synthesized in enantiomerically pure form from (3R,4S)-1-benzyloxy-6-heptene-3,4-diol, prepared from (2E,5E)-1,7-dibenzyloxy-2,5-heptadien-4-ol, employing either Me2AlCl promoted methylative cleavage of (1R,5R,6S)-6-benzyloxy-2,9-dioxabicyclo[3.3.1]nonane or DIBAH promoted reductive cleavage of (1R,5R,6S)-6-benzyloxy-1-methyl-2,9-dioxabicyclo[3.3.1]nonane for the construction of the substituted pyran ring system.