Divergent and Stereocontrolled Synthesis of the Enamide Side Chains of Oximidines I/II/III, Salicylihalamides A/B, Lobatamides A/D, and CJ-12,950
- 28 January 2004
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (4) , 577-580
- https://doi.org/10.1021/ol036381d
Abstract
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 maleimide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.Keywords
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