Synthesis of the Carbocyclic Core of Massadine

被引：11
|
作者：
Sun, Chunrui [1 ]
Lee, Hyunjin [1 ]
Lee, Daesung [1 ]
机构：
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 21期
关键词：
PYRROLE-IMIDAZOLE ALKALOIDS; RELATIVE CONFIGURATION; OROIDIN ALKALOIDS; PALAUAMINE; AXINELLAMINES; STRATEGY; ACCESS; AMINOCYANATION; INTERMEDIATE; CHEMISTRY;
D O I：
10.1021/acs.orglett.5b02709
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The carbocyclic core of massadine has been synthesized relying on a stereoselective formal [3 + 2] cycloaddition of lithiumtrimethylsilyldiazomethane with alpha,beta-unsaturated esters to form a Delta(2)-pyrazoline moiety followed by facile N-N bond cleavage. A unique feature of the current approach is the direct installation of the tertiary alpha-amino center and a beta-cyano group in a cis arrangement on the resulting cydopentane framework via a previously developed formal aminocyanation protocol.
引用
收藏
页码：5348 / 5351
页数：4
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