Asymmetric Synthesis of (+)-Tanikolide and the ß-Methyl-Substituted Analogues of (+)-Tanikolide and (-)-Malyngolide

被引：23

作者：

Doran, Robert ^{[1
]}

Duggan, Lesley ^{[1
]}

Singh, Surrendra ^{[1
,2
]}

Duffy, Colm D. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

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

[2] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 35期

关键词：

Asymmetric synthesis; Zirconium; Lactones; Natural products; MARINE ANTIBIOTIC (-)-MALYNGOLIDE; QUATERNARY CARBON CENTERS; STEREOSELECTIVE-SYNTHESIS; 2,2,5-TRISUBSTITUTED TETRAHYDROPYRAN; ENANTIOCONTROLLED SYNTHESIS; 1,6-ASYMMETRIC INDUCTION; ANTIFUNGAL LACTONE; DOMINO REACTION; (+)-MALYNGOLIDE; ROUTE;

D O I：

10.1002/ejoc.201101190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The d-lactone-containing natural product (+)-tanikolide, a brine shrimp toxin and antifungal compound, was synthesized in nine steps with an overall yield of 26.4?% by employing Sharpless asymmetric epoxidation and ZrCl4-catalyzed intramolecular acetalization as the key steps. The novel beta-methyl-substituted analogues of (+)-tanikolide and()-malyngolide have also been prepared by using the same asymmetric synthetic approach.

引用

页码：7097 / 7106

页数：10

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