86(P20) 海産天然物ミサキノライドAの不斉全合成研究(ポスター発表の部)

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The marine natural product misakinolide A (1), a 40-membered dimeric macrolide iso ated from the Okinawan marine sponge Theonella, has been revealed to exhibit potent cytotoxicity against a variety of human carcinoma cell lines, as well as broad-spectrum antifungal activity. Misakinolide A (1) is structurally charactrized by the C_2-symmetrical dimeric macrolide in which two polypropionate-derived chains including a gigantic lactone ring take axial orientation on a tetrahydropyran ring, and possesses 30 stereogenic centers in total. The unique structure as well as potent anticancer activities of 1 has elicited much attention from synthetic organic chemists, however, its total synthesis has not been achived yet. As part of our synthetic studies toward the polypropionate-derived bioactive compounds possessing characteristic sequences of alternating methyl- and hydroxy-substituted carbons, we set about asymmetric total synthesis of misakinolide A (1). We report here, 1) the enantioselective and highly efficient synthesis of the tetrahydropyran moiety of misakinolide A (1) starting from methyl (S)-lactate (4) which involves the stereoselective intramolecular haloetherification for construction of the tetrahydropyran ring followed by the regioserective reductive ring-opening reaction of an epoxide as key steps; 2) the highly stereoselective synthesis of the polypropionate chain of 1 having 10 stereogenic centers starting from a chiral alcohol 16 which involves the stereospecific methylation of γ,δ-epoxy acrylates as key steps.
天然有機化合物討論会の論文
1999-09-01

86(P20) 海産天然物ミサキノライドAの不斉全合成研究(ポスター発表の部)

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