36 海洋産抗腫瘍性環状ペプチドパテラマイド類の全合成
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The structures of patellamides A, B, and C, cytotoxic lipophilic cyclic peptides from a marine tunicate, were proposed by C.M. Ireland et al to be 1, 2, and 3, respectively, containing unusual fused thiazole-oxazoline units. We synthesized patellamides B and C with proposed structures by the use of diphenyl phosphorazidate (DPPA) and diethyl phosphorocyanidate (DEPC). However, the synthetic peptides with proposed structures 2 and 3 were not identical with natural patellamides B and C, respectively. An inspection of evidences used for the originally assigned structures and a synthetic study on the partial hydrolysate of patellamide B led us to deduce that the structures of patellamides B and C could be reassigned as 8 and 9, respectively, having the reverse order of amino acid residues. This deduction was fully confirmed by the syntheses of patellamides B and C with the revised structures 8 and 9, which were completely identical with natural ones. The structure of patellamide A was analogously revised as 12 by its synthesis. Thus, we could synthetically establish the real structures of patellamides A, B, and C as 12, 8, and 9, respectively.
- 天然有機化合物討論会の論文
- 1985-09-07
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