Enantioselective Total Synthesis of (+)- and (-)-Vittatalactone

被引：5

作者：

Yadav, Jhillu Singh ^{[1
,2
]}

Srinivas, Eedubilli ^{[1
]}

Kumar, Chinta Krinda Suresh ^{[1
]}

Al Ghamdi, Ahmad Al Khazim ^{[2
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ Chem Div 1, Hyderabad 500607, Andhra Pradesh, India

[2] King Saud Univ, Riyadh, Saudi Arabia

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 04期

关键词：

vittatalactone; desymmetrization; Myers asymmetric alkylation; copper-catalyzed alkylation; lactonization; STEREOSELECTIVE-SYNTHESIS; PHEROMONE COMPONENTS; ASYMMETRIC-SYNTHESIS; PRACTICAL SYNTHESIS; SEX-PHEROMONES; ALCOHOLS; FRAGMENT;

D O I：

10.1055/s-0031-1290155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of both enantiomers of (+)- and (-)-vittatalactone has been achieved using a desymmetrization strategy to create three methyl chiral centers. The key steps in these total syntheses are Myers asymmetric alkylation, copper-catalyzed alkylation, 2,2,6,6-tetramethyl-1-piperidinyloxyl-(diacetoxyiodo)benzene [TEMPO-PhI(OAc2)] promoted oxidation and p-toluenesulfonyl chloride mediated lactonization. The products are obtained in good overall yields employing linear synthetic sequences.

引用

页码：628 / 634

页数：7

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