Enantioselective Synthesis of Protected Nitrocyclohexitols with Five Stereocenters. Total Synthesis of (+)-Pancratistatin

被引：39

作者：

Cagide-Fagin, Fernando ^{[1
]}

Nieto-Garcia, Olaia ^{[1
]}

Lago-Santome, Hugo ^{[1
]}

Alonso, Ricardo ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Organ Chem, Santiago De Compostela 15782, A Coruna, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 24期

关键词：

ANTITUMOR ALKALOID (+)-PANCRATISTATIN; OPTICALLY-ACTIVE TETRODOTOXIN; ASYMMETRIC TOTAL-SYNTHESIS; BETA-AZIDONATION REACTION; EFFICIENT TOTAL-SYNTHESIS; AMARYLLIDACEAE CONSTITUENTS; D-GLUCOSE; PANCRATISTATIN; NARCICLASINE; AGENTS;

D O I：

10.1021/jo3022567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Methoxymethylpyrrolidine best performed, among several other proline derivatives, to control the enantioselective [3+3] annulation of beta-(hetero)aryl-alpha-nitro-alpha,beta-enals with commercial 2,2-dimethyl-1,3-dioxan-5-one, a procedure that renders highly oxygenated nitrocyclohexanes endowed with five new stereocenters. Use of this reaction allowed the development of a total synthesis of the antitumoral natural product (+)-pancratistatin; it also converted our previous racemic route to tetrodotoxin into an enantioselective one.

引用

页码：11377 / 11382

页数：6

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