P-38 (-)-Dactylolideの合成研究(ポスター発表の部)

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概要

• 論文の詳細を見る

• (-)-Dactylolide isolated from the Vanuatu sponge Dactylospongia sp. by Riccio and co-workers in 2001 have cytotoxicity toward several tumor cell lines. Zampanolide isolated from Okinawan sponge Fasciospongia rimosa by Tanaka and Higa in 1996 has relative structure. Zampanolide and also show impressive cytotoxicity. The structural features of these compounds are 20 membering macrolactone including cis-2.6-disubstituted tetrahydropyran. We started study of total synthesis of dactylolide for identification of structure-activity relationship. Our synthetic plan was based on couples of two fragments, C1-C8 fragment including Z-trisubstituted diene construction and C9-C20 fragment including cis-2.6-disubstituted tetrahydropyran ring. We could selectively obtain Z-trisubstituted diene 5 from dibromodiene by sonogashira coupling and Kumada-Tamao-Corriu coupling along with inversion of configuration and converted 5 to β-ketophosphonate 8 corresponding to C1-C8 fragment. For the synthesis of C9-C20 fragment, a SnCl_4 promoted the reaction of the C15-C20 fragment 13 prepared conventionally and the C11-C14 fragment 11 prepared by protodesililation of bisallylsilane 10 using PPTS. The coupled alcohol 15 was converted to the ester 17 for the construction of tetrahydropyran ring, followed by treatment with a t-BuOK to afford the desired cis-pyran 19 with a good selectivity. The WHE reaction of 8 with 20 corresponding to C9-C20 fragment proceeded smoothly to afford the ketone 21 possessed of all carbons in the target molecular. dactylolide.

• 天然有機化合物討論会の論文
• 2007-08-24

著者

• 上西 潤一

  Kyoto Pharmaceutical Univ. Kyoto Jpn

• 上西 潤一

  京都薬科大学

• 上西 潤一

  京都薬大

• 河井 伸之

  京都薬大

• 岩本 拓也

  京都薬大

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