STEREOSELECTIVE APPROACH TOWARD OPHIODILACTONES BASED ON AN INTRAMOLECULAR [2+2] CYCLOADDITION REACTION

被引：4
|
作者：
Matsubara, Takaaki [1 ]
Ishihara, Jun [1 ]
Hatakeyama, Susumi [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
来源：
HETEROCYCLES | 2015年 / 90卷 / 01期
关键词：
Baeyer-Villiger Oxidation; 2+2] Cycloaddition; Ketene; Lactone; Natural Product Synthesis; DIPOLAR APROTIC MEDIA; ALPHA-CYANO ESTERS; BETA-KETO-ESTERS; SYNTHETIC APPLICATIONS; MALONATE ESTERS; DEALKOXYCARBONYLATIONS; ALDEHYDES; CHLORIDE; WATER;
D O I：
10.3987/COM-14-S(K)32
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly enantio- and diastereoselective synthesis of a promising precursor of ophiodilactones A and B, tetrameric phenylpropanoids isolated from the ophiuroid Ophiocoma scolopendrina, is described. The synthesis involves an organocatalytic asymmetric Michael reaction, intramolecular [2 + 2] cycloaddition of a ketene to an alkene, Baeyer-Villiger oxidation, and construction of the C2 quaternary center as major transformations.
引用
收藏
页码：405 / 424
页数：20
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