Biomimetic macrocycle-forming Diels-Alder reaction of an iminium dienophile: Synthetic studies directed toward gymnodimine

被引：40

作者：

Johannes, JW ^{[1
]}

Wenglowsky, S ^{[1
]}

Kishi, Y ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 18期

关键词：

D O I：

10.1021/ol051553n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The macrocyclic core of gymnodimine has been constructed via an intramolecular Diels-Alder reaction of an alpha,beta-unsaturated iminium dienophile in water. The cycloaddition furnished a single exo-product, along with two endo-products. Through X-ray analysis of a suitable derivative, the stereochemistry of the exo-product was established, thereby demonstrating that its stereochemistry matches that of gymnodimine. In contrast, macrocyclization of an analogous alpha,beta-unsaturated ketone dienophile gave only undesired endo-products. Interestingly, the imine dienophile shows remarkable stability in water.

引用

页码：3997 / 4000

页数：4

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