Synthesis of Enantiomerically Pure Morphine Alkaloids: The Hydrophenanthrene Route

…, JW Bats, A Werner, J Mulzer

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

Full Text: HTML

Citation Number: 50

Abstract

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 ...

Related Articles:

Selective Olefin Reduction in Thebaine Using Hydrazine Hydrate and O2 under Intensified Continuous Flow Conditions

[Black, T. Howard; Forsee, Jennifer C.; Probst, Donald A. Synthetic Communications, 2000 , vol. 30, # 17 p. 3195 - 3201]

One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal

[Journal of Organic Chemistry, , vol. 74, # 2 p. 747 - 752]

One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal

[Journal of Organic Chemistry, , vol. 74, # 2 p. 747 - 752]

Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-)-and (+)-dihydrocodeinone and (-)-and (+)-morphine

[Hong, Chang Y.; Kado, Noriyuki; Overman, Larry E. Journal of the American Chemical Society, 1993 , vol. 115, # 23 p. 11028 - 11029]

One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal

[Journal of Organic Chemistry, , vol. 74, # 2 p. 747 - 752]

More Articles...