The Journal of organic chemistry

Enantioselective Synthesis of (-)-Dihydrocodeinone: A Short Formal Synthesis of (-)-Morphine1

KA Parker, D Fokas

Index: Parker, Kathlyn A.; Fokas, Demosthenes Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 449 - 455

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Citation Number: 62

Abstract

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 (-)- ...