Vinyl and alkynyl pyrimidines as michael acceptors: an approach to a cylindrospermopsin substructure.
Vinyl and alkynyl pyrimidines as michael acceptors: an approach to a cylindrospermopsin substructure.
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乙烯基和炔基嘧啶作为迈克尔受体：圆柱精蛋白子结构的一种方法。
DOI：
10.1002/chin.200051142
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发表时间：
2000
期刊：
影响因子：
--
通讯作者：
E. Young
中科院分区：
文献类型：
--
作者：
J. F. Djung;D. Hart;E. Young
乙烯基嘧啶9和炔基嘧啶24进行碱基介导的分子内共轭加成反应，其中氨基甲酸酯和尿素分别表现为氮亲核试剂。以2-苯磺酰基-3-苯基氮杂氮杂环丙烷为羟基化试剂，通过金属化-氧化反应将9-环氨基甲酸酯转化为11。用二甲基二氧六环引入C(7)羟基，将来自24的环状尿素转化为圆柱状精浆亚基30。
Vinyl pyrimidine 9 and alkynyl pyrimidine 24 undergo base-mediated intramolecular conjugate addition reactions in which a carbamate and a urea, respectively, behave as nitrogen nucleophiles. The cyclic carbamate derived from 9 was converted to 11 via a metalation-oxidation reaction in which 2-phenylsulfonyl-3-phenyloxaziridine behaves as a hydroxylation reagent. The cyclic urea derived from 24 was converted to cylindrospermopsin substructure 30 using dimethyldioxirane to introduce the C(7) hydroxyl group.