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Communication | Regular issue | Vol 51, No. 7, 1999, pp.1503-1508
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8567
The Reaction of 4,5-Epoxy-2(E)-hexenoate and Secondary Amines, Total Synthesis of (-)-Osmundalactone and (-)-Forosamine

Machiko Ono,* Chikako Saotome, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


A reaction of methy (4R,5R)-4,5-epoxy-2(E)-hexenoate (1) with N-methylbenzylamine gave a diastereomerically pure (3S,4R,5R)-7 and (4S,5R)-8. The former was chemoenzymatically converted to (-)-osmundalactone (12) which is an aglycone of osmundalin. On the other hand, direct conjugated addition of dimethylamine to methyl (4S,5S)-4,5-epoxy-2(E)-hexenoate (1) followed by treatment with MeOH at 40°C exclusively provided (4R,5S)-17 which was converted into L-forosamine (19).