Synthesis of a B/C trans-fused Morphine Structure

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概要

• 論文の詳細を見る

• Hydroboration of Δ^8-desoxycodeine (I) gave a B/C trans-fused morphine derivative, (-)-3-methoxy-8α-hydroxy-4,5α-oxy-N-methylisomorphinan (III) along with two minor products, dihydropseudocodeine (IV) and VII. III, by reaction with p-toluenesulfonyl-chloride gave the 8-p-toluenesulfonate (Vc), which was treated with lithiun aluminum hydride to give (-)-3-methoxy-4,5α-oxy-N-methylisomorphinan (VII). Elimination reaction of Vc with 2,4,6-collidine afforded two double-bond isomers, I and 3-methoxy-4,5α-oxy-Δ^7-N-methylisomorphinan (XII). I gave on hydrogenation the known dihydrodesoxycodeine (XIII). Hydrogenation of XII gave the B/C trans isomer, VII. Some additional studies were made on the hydroboration product (III) and its derivatives to support the B/C trans pentacyclic structure.

• 公益社団法人日本薬学会の論文
• 1965-12-25

著者

• 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.

• 武田 幹男

  田辺製薬株式会社有機化学研究所

• 釘田 博至

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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