119(P62) ポリ環状エーテルの立体選択的合成とその応用(ポスター発表の部)
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The synthetic reaction using functionalized allylstannanes is widely appreciated as one of the most useful methods for the stereocontrolled C-C bond formation. We now report the stereoselective synthesis of functionalized heterocycles via the intramolecular reaction of allylstannane with aldehyde and imine. Stereocontrolled Total Synthesis of Hemibrevetoxin B The treatment of 6 with BF_3・OEt_2 gave 7 as a sole product. Similarly, the intramolecular reaction of 13 derived from 7 proceeded smoothly to give 14. The obtained tetracycle 14 was transformed to hemibrevetoxin B (1) by several steps. Intramolecular Reaction of Imine Derivatives To extend our methodology, we next examined the intramolecular reaction with imine, because the allylation of imine has been well studied as well as that of aldehyde, and such transformation would be an efficient method for the synthesis of cyclic amine derivatives. After several fruitless attempts, we found hydrazones are suitable as a carbon-nitrogen double bond functional group for the intramolecular reaction. The Lewis acid mediated reactions of 16 and 17 gave trans isomers 18a and 19a as a sole product in high to good yields. Stereoselective Synthesis of Hydroxylated Piperidine and Pyrrolidine Derivatives The structural framework of hydroxylated nitrogen heterocycle is widely found in naturally occurring piperidine/pyrrolidine alkaloids such as (-)-desoxoprosophilline and (+)-preussin. We examined the stereoselective synthesis of β-hydroxypiperidine and pyrrolidine derivatives via the intramolecular reaction of 20 and 22. To the best of our knowledge, this is the first example of a successful use of γ-aminoallylstannane in organic synthesis.
- 天然有機化合物討論会の論文
- 1996-09-02
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