A Flexible Approach to Grandisine Alkaloids: Total Synthesis of Grandisines B, D, and F

被引：28

作者：

Kurasaki, Haruaki ^{[2
]}

Okamoto, Iwao ^{[1
]}

Morita, Nobuyoshi ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

[2] Kyorin Pharmaceut Co Ltd, Exploratory Res Labs, Nogi, Tochigi 3290114, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 46期

关键词：

alkaloids; natural products; nitrogen heterocycles; total synthesis; RECEPTOR-BINDING AFFINITY; INDOLIZIDINE ALKALOIDS; ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; ACYLIMINIUM IONS; IMINIUM ION; LEAVES; ACID; CYCLIZATIONS; VINYLSILANES;

D O I：

10.1002/chem.200901843

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article describes in detail the first total synthesis of grandisine alkaloids, grandisines B, D, and F, which show affinity for the human delta-opioid receptor. The key steps in this synthesis are construction of the isoquinuclidinone moiety of 2 by intramolecular imine formation and the tetracyclic ring system of 4 by stereoselective ring closure of the enolate of amine 8 generated by 1,4-addition of ammonia to 9. Synthesis of key intermediate 9 featured a highly stereoselective Bronsted acid mediated Morita-Baylis-Hillman (MBH) reaction via the N-acyl iminium ion.

引用

页码：12754 / 12763

页数：10

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