Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals

被引：31

作者：

Paioti, Paulo H. S. ^{[1
]}

Ketcham, John M. ^{[1
]}

Aponick, Aaron ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 20期

关键词：

OKADAIC ACID; CYCLIZATION; ALKYNES; FUNCTIONALIZATION; HYDROALKOXYLATION; CYCLOADDITIONS; DERIVATIVES; ASSIGNMENT; ALCOHOLS; NITROGEN;

D O I：

10.1021/ol5024954

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel gold-catalyzed synthesis of unsaturated spiroketals that addresses regioselectivity issues commonly reported in metal-catalyzed spiroketalization of alkynes is reported. The reaction sequence is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable in the synthesis of a broad range of spiroketals.

引用

页码：5320 / 5323

页数：4

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