Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.

Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.
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虾毒素和阿德里亚毒素的 ABCDEF 环系统的会聚合成。

DOI:
10.1021/ol026804w
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发表时间:
2002
期刊:
影响因子:
5.2
通讯作者:
T. Nakata
T. Nakata
中科院分区:
化学1区
文献类型:
--
作者:
Keisuke Suzuki;T. Nakata

文献摘要

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[式:见正文] 完成了虾毒素和阿德里亚毒素ABCDEF环系统的聚合合成。这种有效的收敛策略是基于 A 环的乙炔化物和 DEF 环的三氟甲磺酸酯的偶联、炔烃氧化为二酮、分子内二缩醛化以及用 Et3SiH-TMSOTf 立体选择性还原二缩醛。
[formula: see text] The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.