含雙呋喃天然物Squamocin-K之全合成研究;Total Synthesis of Bis-THF Containing Natural Product Squamocin-K

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题名:	含雙呋喃天然物Squamocin-K之全合成研究;Total Synthesis of Bis-THF Containing Natural Product Squamocin-K
作者:	劉駿威;Liu,Jun-Wei
贡献者:	化學研究所
关键词:	番荔枝科;亞甲基繫繩;置換反應;annonaceous acetogenins;Squamocin-K;CM
日期:	2012-07-23
上传时间:	2012-09-11 18:37:20 (UTC+8)
出版者:	國立中央大學
摘要:	本篇論文利用掌性雙烯雙醇化合物1當作起始物合成番荔枝科乙醯化合物(annonaceous acetogenins)中含有相鄰兩個四氫呋喃(adjacent bis-tetrahydrofurans)中心結構的天然物的差向異構物(14S,21S)-bis-epi-Squamocin-K (18)，藉此發展具有相鄰兩個四氫呋喃的番荔枝科化合物之合成方法。本篇利用亞甲基繫繩以及環閉合置換反應建構其中心結構，之後利用交叉置換反應建構兩端的長碳鏈結構，接著使用環內酯15a做為親核試劑，反應得到關鍵產物。最後轉換官能基得到最終產物天然物的差向異構物(14S,21S)-bis-epi-Squamocin-K (18)。To develop a new and efficient synthetic methodology for annonaceous acetogenins, a large family of natural products containing adjacent bis-tetrahydrofurans as the core structure, wechose bis-epimer (14S,21S)-bis-epi-Squamocin-K (18) as our target molecules. The adjacent bis-tetrahydrofurans cores was constructed by using chiral dienediol 1 as the starting material. Methylene acetal was used as the linker to connect dienediol 1, and then ring-closing-metathesis reaction was applied to provide the precursor of the adjacent bis-tetrahydrofurans structure. The cross-metathesis reaction was used to extend the carbon skeleton. The lactone 15a was used as nucleophile and the total synthesis of 14S,21S-bis-epi-Squamocin-K (18) was achieved.
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