| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1988: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1987: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Research Abstract |
1. Synthesis of optically active 3,4-dihydroxy-2-hydroxymethylpyrrolidines(1) trihydroxylated pyrrolidines(1), which possess potent alpha-glycosidase or alpha-mannosidase inhibitory activities, were synthesized stereoselectively from (S)- and (R)-glutamic acid, or D-ribonolactone.
2. Synthesis of (-)-swainsonine and its stereoisomers Stereoselective allylation of the aldehyde(2) derived from trihydroxylated pyrrolidine prepared as mentioned in section 1, followed by hydroboration-oxidation and subsequent mesylation and deprotection gave (-)-swainsonine and its stereoisomers in moderate yields.
3. Synthesis of Geissmann-Waiss lactone(6) Birch reduction of a compound 4 afforded a compound 5, which was terated with BH_3-Me_2S followed by introduction of nitrile group in the primary hydroxy group and conversion into carboxyl group, and subsequent Mitusnobu reaction to invert a stereochemistry of the secondary hydroxy group and lactonization gave 6 in good yield.
4. Synthesis of (2S,3S,4S)-4-amino-2,3-dihydroxyhexanedioic acid derivative(8) cis-Dihydroxylation of unsaturated lactam(7) derived from (R)-pyroglutamic acid, followed by C-1 unit introduction(nitrile group) to primary hydroxyl group, and subsequent hydrolysis by base and ethanolic hydrogen chloride gave 8, which is a component of AI-77-B(gastroprotective substance).
KA
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