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An improved synthesis of the [5.6.7]-tricyclic core of cyrneine B and glaucopine C
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2020-08-25 , DOI: 10.1039/d0qo00758g
Guo-Jie Wu 1, 2, 3, 4, 5 , Xiu Han 5, 6, 7, 8
Affiliation  

A new route for the synthesis of the [5.6.7]-tricyclic core structure of cyrneine B and glaucopine C is presented. The key transformations included an efficient Suzuki cross-coupling of the densely substituted cyclopentenyl triflate with cyclic vinylboronate and a highly regio- and stereoselective intramolecular deconjugative alkylation. The synthetic route allowed for the construction of the [5.6.7]-tricyclic core within a 16-step linear sequence from the commercially available 2-methylcyclopentanone, which is five steps shorter than the first generation route as reported previously by us.

中文翻译:

胱氨酸B和青藤碱C的[5.6.7]-三环核的合成方法改进

提出了一条新的路线,用于合成[5.6.7]-三聚氰胺乙炔和青草碱C的三环核心结构。关键的转化包括稠密取代的环戊烯基三氟甲磺酸酯与环状乙烯基硼酸酯的高效Suzuki交叉偶联以及高度区域和立体选择性的分子内去共轭烷基化。合成途径允许在16步线性序列中由市售的2-甲基环戊酮构建[5.6.7]三环核心,该序列比我们先前报道的第一代途径短五步。
更新日期:2020-09-30
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