Synthetic studies toward penitrem E: enantiocontrolled construction of B-E rings

Synthetic studies toward penitrem E: enantiocontrolled construction of B-E rings
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Penitrem E 的合成研究:B-E 环的对映体控制结构

DOI:
10.1039/c4cc08505a
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发表时间:
2015
影响因子:
4.9
通讯作者:
and Hidetoshi Tokuyama
and Hidetoshi Tokuyama
中科院分区:
化学2区
文献类型:
--
作者:
Yu Yoshii;Takanori Otsu;Norihiko Hosokawa;Kiyosei Takasu;Kentaro Okano;and Hidetoshi Tokuyama

文献摘要

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以4-碘吲哚为原料,共13步完成了对映体控制的苯醚B-E环的合成,总收率为1.7%。由tf2nh催化的非对映选择性(2+2)-环加成反应在硅烯醇醚和丙烯酸甲酯之间生成了具有环丁烷特征的四环产物。
Enantiocontrolled construction of B–E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cyclobutane ring bearing a hydroxyl group.