64520-24-7Relevant articles and documents
Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine
Parker, Kathlyn A.,Fokas, Demosthenes
, p. 449 - 455 (2007/10/03)
The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b → (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials.
Studies in the (+)-morphinan series. 7. Unusual crystallographic and tautomeric properties of (+)-4-hydroxy-7-oxo-3-methoxy-17-methyl-5,6-dehydromorphinan: An interlacing double helix
Minamikawa,Rice,Jacobson,et al.
, p. 1901 - 1905 (2007/10/02)
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