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

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概要

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• 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-Δ^7-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-Δ^7-N-methylisomorphinan (XIX). Demethylation of XIII gave the title compound (XXII).

• 公益社団法人日本薬学会の論文
• 1970-08-25

著者

• 井上 博純

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 釘田 博至

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 釘田 博至

  田辺製薬有機研究所

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 釘田 博至

  Organic Chemistry Research Laboratory:tanabe Seiyaku Co. Ltd.

• 井上 博純

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .

• 釘田 博至

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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