Enantioselective photocycloaddition mediated by chiral Bronsted acids: Asymmetric synthesis of the rocaglamides
Enantioselective photocycloaddition mediated by chiral Bronsted acids: Asymmetric synthesis of the rocaglamides
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DOI：
10.1021/ja062621j
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发表时间：
2006-06-21
影响因子：
15
通讯作者：
Porco, John A., Jr.
中科院分区：
文献类型：
--
作者：
Gerard, Baudouin;Sangji, Sheharbano;Porco, John A., Jr.
概述了罗卡格酸甲酯和相关天然产物罗卡格酰胺和罗卡格醇的对映选择性合成。该方法涉及由手性布朗斯台德酸 (TADDOL) 促进的对映选择性 [3 + 2] 光环加成反应，得到 aglalain 前体，然后通过酮醇转移/还原序列到达罗卡格特核心。
Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core.