Tetrahedron

Biomimetic total synthesis of (−)-codeine

JD White, G Caravatti, TB Kline, E Edstrom, KC Rice…

文献索引：White; Caravatti; Kline; et al. Tetrahedron, 1983 , vol. 39, # 14 p. 2393 - 2397

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被引用次数: 53

摘要

The opium alkaloid (−)-codeine was synthesized in eight steps from (±)-N-norreticuline R-(−)- norreticuline, obtained by resolution, was converted to (R)-N-trifluoroacetyl-6'- bromonorreticuline and the latter was subjected to phenolic oxidative coupling with a variety of aryliodoso complexes in dichloromethane. N-Trifluoroacetyl-1-bromonorsalutaridine prepared by this means was transformed to 1-bromosalutaridinol (as a mixture of epimers) ...