Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

被引：11

作者：

Yadav, Jhillu S. ^{[1
]}

Rao, Ragam Nageshwar ^{[1
]}

Kumar, Begari Prem ^{[1
]}

Somaiah, Ragam ^{[1
]}

Ravindar, Kontham ^{[1
]}

Reddy, Basi V. Subba ^{[1
]}

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

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] King Saud Univ, Riyadh 11451, Saudi Arabia

来源：

SYNTHESIS-STUTTGART | 2011年 / 19期

关键词：

lactones; Wittig olefination; Sharpless asymmetric epoxidation; intramolecular hydride transfer; syn-aldol; GAMMA-BUTYROLACTONES; (+)-TRANS-WHISKEY LACTONE; STEREOSELECTIVE-SYNTHESIS; ROUTE; (+)-ELDANOLIDE; ENANTIOMERS; CYCLIZATION; RESOLUTION;

D O I：

10.1055/s-0030-1260190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and concise stereoselective total synthesis of naturally occurring (-)-cis-aerangis lactone and (-)-cis-cognac lactone is described. The Sharpless asymmetric epoxidation of a primary allylic alcohol and TBSOTf-mediated intramolecular hydride transfer of a chiral epoxy alcohol have been successfully utilized for the construction of a key precursor with syn-aldol stereochemistry using a non-aldol pathway.

引用

页码：3168 / 3172

页数：5

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