Prins-Type Cyclization Reactions in Natural Product Synthesis

被引：177

作者：

Han, Xun ^{[1
]}

Peh, GuangRong ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 07期

基金：

美国国家卫生研究院;

关键词：

Synthetic methods; Natural products; Cyclization; Oxygen heterocycles; Diastereoselectivity; Carbocations; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PETASIS-FERRIER UNION/REARRANGEMENT; OXIDATIVE CARBOCATION FORMATION; FORMAL TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; METHOXYCARBENIUM IONS; LEUCASCANDROLIDE-A; BRYOSTATIN ANALOGS; COPE; NEOPELTOLIDE;

D O I：

10.1002/ejoc.201201557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Prins-type cyclization reactions proceed through the intramolecular addition of a pi-nucleophile to an oxocarbenium ion or related species to generate a ring through carbon-carbon bond formation, often with excellent and predictable stereocontrol. The widespread presence of naturally occur-ring oxygen-containing heterocycles has made these reactions exceedingly valuable for total synthesis efforts. This microreview covers several common variations of Prins-type cyclizations and highlights their applicability to the total synthesis of natural products and analogs.

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页码：1193 / 1208

页数：16

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