136(P-88) ボンクレキン酸の合成研究(ポスター発表の部)

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Bongkrekic acid is a toxic antibiotic produced by the microorganism Pseudomonas cocovenenans. The high toxicity of bongkrekic acid has been attributed to its affinity for the ATP / ADP translocator protein residing in the mitochondrial inner membrane, thus preventing oxidative phosphorylation. Recently, bongkrekic acid has been found to be an inhibitor of apoptosis acting on permeability transition pores. Thus, bongkrekic acid is very important and a useful biochemical tool for investigation of apoptosis. Since it is, however, difficultly available by fermentation and there has been only one report of chemical synthesis, an efficient synthetic method for bongkrekic acid has been required. Herein, we report the synthetic studies on bongkrekic acid. Our plan for synthesis of bongkrekic acid is a convergent strategy. Bongkrekic acid is devided into the right-hand segment and the left-hand segment. The synthesis of the right-hand segment is as follows: Evans' asymmetric alkylation provided 13 with 94:6 diastereoselectivity. After removal of the chiral auxiliary, Takai's alkenylation of the aldehyde 14, followed by Suzuki coupling, provided the triene 17, which was converted into the right-hand segment 19. The left-hand segment was synthesized as follows: The known O-trityl-(S)-umbelactone, prepared from D-mannitol in good yields, was reduced by DIBAH to give the lactol, which was subjected to Wittig olefination to afford hydroxy-(Z,E)-diene 27 as a single isomer. After conversion of 27 into epoxide 29, the acetylide of 31 reacted with 29 in the presence of BF_3・OEt_2 to furnish the C11-C22 backbone, which was converted into the right-hand segment 34.
天然有機化合物討論会の論文
2000-10-01

136(P-88) ボンクレキン酸の合成研究(ポスター発表の部)

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