108(P38) 抗腫瘍活性物質ムコシンの全合成(ポスター発表の部)

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Mucocin (1), which was isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is the first annonaceous acetogenin to be reported that bears a hydroxylated tetrahydropyran ring along with a tetrahydrofuran ring, and shows a powerful antitumor activity. Here, we report the first total synthesis of 1 employing carbohydrates as a key starting material. Our synthetic strategy was based on the convergent process involving a sequential coupling reaction of three building blocks such as 2, 3, and 4 (Scheme 1). Initially, tetrahydropyranyl aldehyde 2 was prepared from D-galactose (5) via β-selective C-glycosidation, and a tetrahydrofuran derivative 3 was stereoselctively synthesized through a chelation-controlled addition of ethynyl group to the 2,5-anhydro-D-mannitol derivative 13. These fragments were coupled in the presence of cerium chloride to provide 15 in good yield. After hydrogenation, simple two-step oxidation-reduction sequence of the corresponding saturated compounds gave the desired isomer 16 in high diastereoselectivity (16/17=97/3). This was converted into the acetylene derivative 20. On the other hand, construction of an α-substituted γ-lactone moiety 27 corresponding to the C_1-C_9 fragment of 1 was achieved by taking advantage of radical cyclization of an acyclic phenylselenocarbonate 4 derived from L-rhamnose (7) as shown in Scheme 5. Finally, a palladium-catalyzed cross coupling reaction of 20 and 27, and subsequent two-step sequence led to mucocin (1).
天然有機化合物討論会の論文
1998-08-31

108(P38) 抗腫瘍活性物質ムコシンの全合成(ポスター発表の部)

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