65 生理活性ペプチド構成新アミノ酸類、ガランチニン酸及びデトキシニンの合成

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Unusual amino acids, galantinic acid and N-t-Boc derivative of detoxinine were synthesized stereoselectively from (2R)-2-amino-3-butenol (6a) and 2-amino-4-pentenoic acid (7a), respectively. (A) Synthesis of (+)-galantinic acid (3), a constituent amino acid in peptide antibiotics galantin I (1). (a) Epoxidation of 6b with MCPBA afforded exclusively the epoxy alcohol (2S, 3S) 9b. (b) Introduction of vinyl moiety to 9c was achieved using divinylcuprate 10 (9c→12+13). (c) The synthesis confirmed the absolute configuration of natural 3. (B) Detoxinine (4), a constituent in detoxin D_1 (2) possesses a selective antagonistic activity of blasticidin S; Synthesis of N-t-Boc-detoxinine (42). (a) Sharpless oxidation (SeO_2/t-BuOOH) of 7b afforded stereoselectively threo-2-amino-3-hydroxy-4-pentenoic acid 21 (21:22=75:25). (b) Aldol condensation of the aldehyde 30 with lithium enolate of t-butyl acetate showed remarkable selectivity to give 31 (31:32=85:15). (c) Two types of novel pyrrolidine ring formation were accomplished (26→27 and 39→40).
天然有機化合物討論会の論文
1983-09-15