Microwave-Assisted Synthesis of Substituted Tetrahydropyrans Catalyzed by ZrCl4 and Its Application in the Asymmetric Synthesis of exo- and endo-brevicomin

被引：32

作者：

Singh, Surendra ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, UCD Conway Inst, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

WESTERN PINE-BEETLE; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; PHEROMONE SYNTHESIS; CYCLIZATION; (+)-EXO-BREVICOMIN; ENANTIOMERS; (-)-ENDO-BREVICOMIN;

D O I：

10.1021/jo901019u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ZrCl4-catalyzed deprotection of 1,3-dioxane/dioxalane and the simultaneous formation of 6-methoxy-substituted tetrahydropyrans proceeded under microwave irradiation in good yield. This synthetic methodology was used for the asymmetric synthesis of (+)-exo- and (+)-endo-brevicomin in 55% overall yield over 4 steps.

引用

页码：5758 / 5761

页数：4

共 45 条

[11]

Florke H, 1996, SYNTHESIS-STUTTGART, P647

[12]

Gallos JK, 2001, HETEROCYCLES, V55, P781

[13]

Grieco P.A., 1978, TETRAHEDRON LETT, V19, P419

[14]

Hanessian S., 1983, Total Synthesis of Natural Products: TheChiron Approach