Synthesis of B/C trans-Fused Morphine Structures. IV. Synthesis of B/C trans-Isomorphine

Acetylation and subsequent oxidation of the organoborane intermediate obtained from hydroboration of isoneopine (III) gave (-)-3-methoxy-6β-acetoxy-8α-hydroxy-4, 5α-epoxy-N-methylisomorphinan (IV). Hydroboration of isoneopine-(N-n-butyl)-carbamate (XIV) gave the 6β-(N-n-butyl)-carbamoyloxy-8α-hydrox...

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Published inChemical & pharmaceutical bulletin Vol. 18; no. 8; pp. 1569 - 1575
Main Authors INOUE, HIROZUMI, TAKEDA, MIKIO, KUGITA, HIROSHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1970
Japan Science and Technology Agency
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Summary:Acetylation and subsequent oxidation of the organoborane intermediate obtained from hydroboration of isoneopine (III) gave (-)-3-methoxy-6β-acetoxy-8α-hydroxy-4, 5α-epoxy-N-methylisomorphinan (IV). Hydroboration of isoneopine-(N-n-butyl)-carbamate (XIV) gave the 6β-(N-n-butyl)-carbamoyloxy-8α-hydroxy derivative (XV). (-)-3-Methoxy-6β-hydroxy-4, 5α-epoxy-Δ7-N-methylisomorphinan (XIII, B/C trans-isocodeine) was synthesized from either IV or XV via elimination of the respective 8α-tosyloxy derivatives (VI and XVI). XIII was also obtained by solvolysis of (+)-3-methoxy-6α-tosyloxy-4, 5α-epoxy-Δ7-N-methylisomorphinan (XIX). Demethylation of XIII gave the title compound (XXII).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.18.1569