A short and efficient asymmetric synthesis of (-)-frontalin, (-)-exo-isobrevicomin and a volatile contributor of beer-aroma

被引：17

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：

TETRAHEDRON | 2010年 / 66卷 / 30期

关键词：

MOUNTAIN PINE-BEETLE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; KINETIC RESOLUTION; ENANTIOMERS; FRONTALIN; PHEROMONE; CYCLOADDITIONS; IDENTIFICATION; COMPONENTS;

D O I：

10.1016/j.tet.2010.05.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural products, (-)-frontalin and (+)-exo-isobrevicomin were synthesized employing Sharpless asymmetric epoxidation and ZrCl4-catalyzed intramolecular acetalization as the key steps. (-)-Frontalin was synthesized in three steps with a 61.4% overall yield and 89.9% ee and (-)-exo-isobrevicomin also obtained in an overall satisfactory yield of 10.1% and 97% ee. We have also synthesized the volatile contributor of beer aroma in a 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5701 / 5706

页数：6

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