Temporary restraints to overcome steric obstacles: an efficient strategy for the synthesis of mycalamide B.

Temporary restraints to overcome steric obstacles: an efficient strategy for the synthesis of mycalamide B.
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克服空间障碍的临时限制:合成 mycalamide B 的有效策略。

DOI:
10.1002/anie.201003361
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发表时间:
2010
期刊:
Angewandte Chemie (International ed. in English)
影响因子:
--
通讯作者:
Rawal,VireshH
Rawal,VireshH
中科院分区:
--
文献类型:
--
作者:
Jewett,JohnC;Rawal,VireshH

文献摘要

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抑制与释放:报道了咪卡拉酰胺B的高效合成。该合成路线具有以下特点:(a)一罐Mukaiyama-Michael /环氧化序列引入天然产物中发现的三个立体中心,(b)分子内异氰酸酯捕获产生刚性的10元环氨基甲酸酯,以及(c)环氨基甲酸酯选择性打开以显示完整构建的天然产物。
Restrain and Release: An efficient synthesis of mycalamide B is reported. The synthetic route features (a) a one-pot Mukaiyama–Michael/epoxidation sequence to introduce three of the stereocenters found in the natural product, (b) an intramolecular isocyanate trapping to produce a rigid 10-membered cyclic carbamate, and (c) the selective opening of the cyclic carbamate to reveal the fully constructed natural product.