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New developments in asymmetric Bradsher cycloadditions: use of chiral dienes

โœ Scribed by Dominique Urban; Eric Duval; Yves Langlois


Book ID
104211255
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
120 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Several serinol derivatives have been prepared and condensed following the Zincke reaction with 2,7-naphthyridine. The resulting naphthyridinium salts were engaged in Bradsher cycloadditions with enol ethers and afforded tetracyclic adducts, potential synthetic precursors of manzamine A alkaloid.


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## Abstract Some novel Dielsโ€Alder reactions of the opium alkaloid (โˆ’)โ€thebaine (1) as an electronโ€rich diene and a reinvestigation of its reactions with cyclic and acyclic dienophiles are described. The ฯ€โ€facial selectivity has been studied on the basis of structural analyses of the cycloadducts.