P-70 腫瘍細胞増殖阻害活性マクロライド・ハテルマライドNAメチルエステルの合成とビセライド類の合成研究(ポスター発表の部)

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Biselides A, B, C, D, and E, oxygenated analogs of haterumalides, were isolated from the Okinawan ascidian Didemnidae sp. by our group. Biselides A (1), B (2) and haterumalide NA methyl ester (3) showed cytotoxicity against human cancer cells. Although biselides A (1), B (2) and haterumalide NA methyl ester (3) are cytotoxic, they are less toxic against brine shrimp than haterumalide NA. We planned the practical synthesis of haterumalides and biselides by Suzuki-Miyaura cross coupling between the tetrahydrofuran and alkenylsilane units and construction of the vinyl chloride part via stereoselective chlorination of an alkenylsilane. Synthesis of the C5-C15 segment (5) started from D-mannose. Terminal olefin compound was prepared in the efficient ten-step sequence. Hydroboration of the terminal olefin compound with 9-BBN dimer followed by addition of a catalytic amount of PdCl_2(dppf) and an alkenylsilane afforded the desired coupling compound. The coupling compound was subjected to stereoselective chlorination by NCS and K_2CO_3 to a chloroolefin compound. Treatment of the chloroolefin compound under acidic conditions gave the C5-C 15 segment (5). Oxidation of 5 by Dess-Martin periodinane afforded a labile aldehyde, which was converted into the Z-conjugated ester 6 by using the Ando-modified Horner-Wadsworth-Emmons reaction. After 9 steps, the macrolactonization of 10 was accomplished by the Yamaguchi method to give the desired lactone 11. After 5 steps, we achieved the construction of the key intermediate in our previous synthesis. This approach improved the yield of 3 in the previous work. Futher approach to the synthesis of bidelides is currently underway in our group and will be reported in the symposium.
天然有機化合物討論会の論文
2007-08-24

P-70 腫瘍細胞増殖阻害活性マクロライド・ハテルマライドNAメチルエステルの合成とビセライド類の合成研究(ポスター発表の部)

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