A concise synthesis of paraconic acids: (-)-methylenolactocin and (-)-phaseolinic acid

被引：20
作者：
Fernandes, Rodney A. [1 ]
Chowdhury, Asim K. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 10期
关键词：
BUTYROLACTONE NATURAL-PRODUCTS; METHYLENE-GAMMA-BUTYROLACTONES; RING-CLOSING METATHESIS; ONE-CARBON SOURCE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; (+)-NEPHROSTERANIC ACID; (+)-TRANS-WHISKEY LACTONE; CLAISEN REARRANGEMENT; FORMAL SYNTHESIS;
D O I：
10.1016/j.tetasy.2011.05.007
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A concise synthesis of (-)-methylenolactocin and (-)-phaseolinic acid, the common members of the paraconic acids, is described. The synthesis is based on regioselective asymmetric dihydroxylation and the orthoester Johnson-Claisen rearrangement of allyl alcohol with a vicinal diol functionality as the key steps. The synthesis was completed in 10 steps with overall yields of 4.1% for (-)-methylenolactocin and 4.3% for (-)-phaseolinic acid. (C) 2011 Elsevier Ltd. All rights reserved.
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收藏
页码：1114 / 1119
页数：6
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