Synthesis of a B/C trans-fused Morphine Structure

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Abstract
Hydroboration of delta8-desoxycodeine (I) gave a B/C trans-fused morphine derivative, (-)-3-methoxy-8[alpha]-hydroxy-4,5[alpha]-oxy-N-methylisomorphinan (IK) along with 2 minor products, dihydropseudocodeine (IV) and VII. m, by reaction with p-toluenesulfonylchloride gave the 8-p-toluenesulfonate (Vc), which was treated with lithiun aluminum hydride to give (-)-3-methoxy-4,5[alpha]-oxy-N-methyl -isomorphinan (Vn). Elimination reaction of Vc with 2,4,6-collidine afforded two double-bond isomers, I and 3-methoxy-4,5[alpha]-oxy delta7-N-methylisomorphinan (XII). I gave on hydrogenation the known dihydrodesoxycodeine (XHI). Hydrogenation of XII gave the B/C trans isomer, VTI. Some additional studies were made on the hydroboration product (HI) and its derivatives to support the B/C trans pentacyclic structure.

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