Syntheses of Morphin-like Structures. III. Stereochemical Control of Addition of Borane to 9-Methylenebenzomorphan
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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).
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 12 (10), 1166-1171, 1964
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204173814400
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- NII論文ID
- 110003619302
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- PubMed
- 14241631
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可