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Communication | Special issue | Vol 54, No. 1, 2001, pp.69-72
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)27
Concise Synthesis of (3R,4S)-3-hydroxy-4-methyl-γ-butyrolactone

Takashi Nishiyama, Toshiko Nishioka, Tomoyuki Esumi, Yoshiharu Iwabuchi, and Susumi Hatakeyama*

*Faculty of Pharmaceutical Sciences, Nagasaki 852-8521, Japan


A three-step sequence involving highly stereoselective deconjugation of ethyl (E)-2-pentenoate, osmylation, and resolution by lipase-catalyzed enzymatic acetylation allowed an extremely expeditious synthesis of (3R,4S)-3-hydroxy-4-methyl-γ-butyrolactone with 90% ee, from which (—)-blastmycinolactol and (+)-blastmycinone were synthesized.