硝基
化学
环加成
分子内力
烯烃纤维
立体化学
全合成
分子内反应
有机化学
催化作用
作者
Peter M. Wovkulich,Milan R. Uskoković
出处
期刊:Tetrahedron
[Elsevier]
日期:1985-01-01
卷期号:41 (17): 3455-3462
被引量:92
标识
DOI:10.1016/s0040-4020(01)96700-6
摘要
A total synthesis of daunosamine (3) and acosamine (4) has been accomplished via a diastereoselective intramolecular nitrone-olefin cyclization. In the key step the chiral nitrone 12a cyclized to give two isoxazolidines 13a and 14a in an 82:18 ratio. Further elaboration of 13a led to daunosamine and acosamine. The effects of olefin substitution on the diastereoselectivity of the cycloaddition was also examined.
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