Syntheses of Morphin-like Structures. III. Stereochemical Control of Addition of Borane to 9-Methylenebenzomorphan

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概要

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• The addition of borane to 9-methylenebenzomorphan at high temperature has been examined in the hope of clarifying stereochemical course of the hydroboration which gave selectively the 9β-hydroxymethyl derivative in the previous study. Reaction of pyridine-borane with I in benzene at 70° gave the benzomorphan-borane (II) in high yield. Heating II in anisole followed by the oxidation gave the 9α-hydroxymethyl derivative (IV) along with the 9βisomer and a neutral product (V). The formation of 9α isomer was rationalized in terms of the dissociation of the amine-borane prior to the addition of borane to the double bond. α-Orientation of the 9-hydroxymethyl group of IV was established by converting IV to the known dl-2,5,9α-trimethylbenzomorphan (VIII) via the toluene-p-sulfonate (VII).

• 公益社団法人日本薬学会の論文
• 1964-10-25

著者

• 武田 幹男

  Osaka Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 釘田 博至

  Osaka 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.

• 釘田 博至

  Osaka Research Laboratory Gohei Tanabe & Co. Ltd.

• 武田 幹男

  田辺製薬株式会社有機化学研究所

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