144318-24-1Relevant 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.
Convergent synthesis of (±)-dihydroisocodeine in 11 steps by the tandem radical cyclization strategy. A formal total synthesis of [±)-morphine
Parker,Fokas
, p. 9688 - 9689 (2007/10/02)
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