45 エリスリナアルカロイドの合成研究 : Erysotramidine,3-Epierysotramidine 3-Epi-8-oxoerythralineの合成
書誌事項
- タイトル別名
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- 45 SYNTHETIC STUDIES OF ERYTHRINA ALKALOID : Synthesis of Erysotramidine, 3-Epierysotramidine and 3-Epi-8-oxoerythraline
- 公開日
- 1980
- DOI
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- 10.24496/tennenyuki.23.0_343
- 公開者
- 天然有機化合物討論会実行委員会
説明
An efficient synthesis of Erythrina alkaloid was described. 1. Synthesis of isoquinolinopyrrolinedione 5. The synthesis of 5 was achieved starting from arylethylamine 6 in yield of 60〜80% by following three steps: i) Condensation with ethyl or methyl malonyl chloride. ii) Intramolecularcyclization to isoquinoline. iii) Condensation with oxalyl chloride. 2. Diels-Alder Reaction of 5 with butadienes. Diels-Alder addition of 5 with butadienes, specially 1-methoxy-3-silyloxybutadiene or 1,3-disilyloxybutadiene, smoothly proceeded in a regio and stereospecific manner to give 1,4-adducts 12 and 13, respectively, having an erythrinan skelton. The structures were elucidated by the X-ray analysis of the diacetate 20 derived from 12c. 3. Syntheses of erysotramidine 2,3-epierysotramidine 28, 8-oxoerythraline 35 and 3-epi-8-oxoerythraline 34. The value of this approach to Erythrina alkaloid was demonstrated by the total synthesis of 2 and its epimer 28. Partial reduction of 12b or 13b with LiBH_4, followed by acidic treatment afforded a conjugated ketone 22. Decarboalkoxylation of 22 with MgCl_2 in DMSO gave a dienone 24. Reduction of this with NaBH_4 gave epimeric allyl alcohols 25 and 26, which on methylation with CH_3I furnished 3-epierysotramidine 28 and erysotramidine 2, respectively. 8-Oxoerythraline 35 and its 3-epimer 34 were also synthesized from the key intermediate 13c by similar procedure.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 23 (0), 343-350, 1980
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390282681049538944
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- NII論文ID
- 110006678161
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可