スルガトキシン合成に関するモデル実験(第4報)脱水型スルガトキシンの骨格形成その1

概要

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Unexpected results in the initial experiments for the construction of the pentacyclic surugatoxin framework from debromo-nitro-ketone 9 are described in this paper. Treatment of 9 with pyruvoyl chloride in pyridine gave nitro-enol lactone 10 which was reduced with Zn/AcOH to give amino-enol lactone 11. When a solution of 11 in CH_2Cl_2 was kept at room temperature, 11 was gradually decomposed to tetrahydropteridine 13. On the other hand, 9 was transformed to amide 16 by the sequence 1) conversion to methoxymethyl enol ether 14 by the treatment with K_2CO_3 in N, N-dimethylformamide and subsequent reaction with chloromethyl methyl ether, 2) reduction of the nitro group to amine 15 (Zn/AcOH), and 3) acylation of 15 with 2-methoxyacrylic acid-dicyclohexylcarbodiimide. When 16 was treated with 20% trifluoroacetic acid in CH_2Cl_2,unexpected ring closure occurred to form tetrahydropteridine 18.
社団法人日本薬学会の論文
1985-04-25