Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals

被引：117

作者：

Aponick, Aaron ^{[1
]}

Li, Chuan-Ying ^{[1
]}

Palmes, Jean A. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 01期

关键词：

CHEMISTRY; CONSTITUENTS; SPIROACETALS; AVERMECTINS; POLYETHER; KETONES; ALKYNES; ROUTE;

D O I：

10.1021/ol802491m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-BU)(2)(o-biphenyI)]Cl and AgOTf is employed in THF at 0 degrees C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.

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收藏

页码：121 / 124

页数：4

相关论文

共 36 条

[1] Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].

Aho, JE ;

Pihko, PM ;

Rissa, TK .

CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440

[2] REACTION OF COPPER ENOLATES OF ESTERS WITH PROPARGYLIC SYSTEMS - FACILE PREPARATION OF 3,4-DIENOIC ESTERS, STEREOSELECTIVE REARRANGEMENT TO (2E,4Z)-DIENOIC AND (2E,4E)-DIENOIC ESTERS, AND STEREOSELECTIVE SYNTHESIS OF A FRAGRANCE FROM BARTLETT PEAR [J].

AMOS, RA ;

KATZENELLENBOGEN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :555-560

[3] Au-catalyzed cyclization of monoallylic diols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Biannic, Berenger .

ORGANIC LETTERS, 2008, 10 (04) :669-671

[4] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[5] CHEMISTRY OF BIS-SPIROACETALS - SYNTHESIS OF THE 1,6,8-TRIOXADISPIRO[4.1.5.3]PENTADECANE RING-SYSTEM [J].

BAKER, R ;

BRIMBLE, MA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (01) :125-131

[6] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[7] Palladium mediated spiroketal synthesis: application to pheromone synthesis [J].

Conway, JC ;

Quayle, P ;

Regan, AC ;

Urch, CJ .

TETRAHEDRON, 2005, 61 (50) :11910-11923

[8] A NEW STRATEGY FOR THE SYNTHESIS OF SPIROKETALS [J].

DANISHEFSKY, SJ ;

PEARSON, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) :3865-3866

[9] The chemistry of trichlorosilyl enolates. Aldol addition reactions of methyl ketones [J].

Denmark, SE ;

Stavenger, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (37) :8837-8847

[10] PtCl4-catalyzed domino synthesis of fused bicyclic acetals [J].

Dieguez-Vazquez, Alejandro ;

Tzschucke, C. Christoph ;

Lam, Wing Yee ;

Ley, Steven V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :209-212

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