Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition
Using an intramolecular nitrone cycloaddition and a Heck cyclization as the crucial transformations, a total synthesis of the racemic morphine alkaloid thebainone A was accomplished in 22 steps commencing with isovanillin.
Improved synthesis of dihydrothebainone and its 14 β-epimer
An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Φ (4) to thebainone-A (6) with 6N HCl.
Davidson,Gregg
p. 547 - 558
(2007/10/03)
A novel approach to the synthesis of morphine alkaloids: The synthesis of (d,l)-thebainone-A
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Tius,Kerr
p. 5959 - 5966
(2007/10/02)
Synthesis of 7,8-didehydro-3,4-dimethoxy-17-methylmorphinan-6-one and the regioselective reduction of the keto function
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Van Gurp,Lie,Mense,Maat
p. 325 - 329
(2007/10/02)
Elimination of the 4-hydroxyl group of the alkaloids related to morphine. 8. Synthesis of (-)-3-methoxy-N-methylisomorphinan derivatives.