Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950

被引:77
作者
Coleman, RS [1 ]
Liu, PH [1 ]
机构
[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA
关键词
D O I
10.1021/ol036381d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)and (Z)-vinyl iodides with a protected malelmide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.
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页码:577 / 580
页数:4
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