Synthesis of Enantiomerically Pure Morphine Alkaloids: The Hydrophenanthrene Route

…, JW Bats, A Werner, J Mulzer

文献索引：Trauner, Dirk; Bats, Jan W.; Werner, Andreas; Mulzer, Johann Journal of Organic Chemistry, 1998 , vol. 63, # 17 p. 5908 - 5918

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被引用次数: 50

摘要

A concise, linear, total synthesis of (-)-dihydrocodeinone a close synthetic precursor of (-)- codeine and (-)-morphine has been achieved. The carbocyclic core of the alkaloid was provided in the form of a phenanthrenone, which was resolved by chromatography on cellulose triacetate. A cuprate conjugate addition was used to establish the crucial benzylic quaternary stereocenter and to introduce the C2-side chain. Dimeric byproducts provide ...