The Reaction of (4R, 5R)-and (4S, 5S)-4, 5-Epoxy-2(E)-Hexenoates and Secondary Amines

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概要

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• A reaction of methyl (4R, 5R)-4, 5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R, 5R)-4, 5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S, 5R)-4-N-benzylmethylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which is an aglycone of osmundalin. On the other hand, the directly conjugated addition of dimethylamine to methyl (4S, 5S)-4, 5-epoxy-2(E)-hexenoate 1 followed by treatment with MeOH at 40℃ exclusively provided methyl (4R, 5S)-4-dimethylamino-5-hydroxy-2(E)-hexenoate 16, which was converted into L-(-)-forosamine 18.

• 公益社団法人日本薬学会の論文
• 2001-07-01

著者

• AKITA Hiroyuki

  School of Pharmaceutical Science, Toho University

• Akita H

  Toho Univ. Chiba Jpn

• Akita Hiroyuki

  School Of Pharmaceutical Science Toho University

• ONO Machiko

  School of Pharmaceutical Sciences, Toho University

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• SAOTOME Chikako

  School of Pharmaceutical Sciences, Toho University

• Saotome C

  Mitsubishi Kagaku Inst. Life Sci.(mitils)

• Saotome Chikako

  School Of Pharmaceutical Science Toho University

• Ono M

  School Of Pharmaceutical Sciences International University Of Health And Welfare

• Ono Machiko

  School Of Pharmaceutical Sciences Toho University

• Ono Machiko

  School Of Pharmaceutical Sciences International Univ. Of Health And Welfare

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