21 ヒガンバナ科アルカロイド、(±)-リコリンの合成(口頭発表の部)
書誌事項
- タイトル別名
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- 21 A SYNTHESIS OF AMARYLLIDACEAE ALKALOID, (±)-LYCORINE
説明
In our continuing studies of synthesis of Amaryllidaceae alkaloids, an alternative synthesis of (±)-lycorine was accomplished. Intramolecular Diels-Alder reaction of triene-ester(6) gave cis-δ-lactone(7a) in 86% yield, which was converted to 10 in six steps. Jones oxidation of 10, followed by Curtius rearrangement afforded a carbamate(12), which was treated with TFA and succesively with NaOMe to give 13 in good yield. Epoxidation of t-butyldimethylsilyl ether of 13 proceeded stereoselectively to give 16 as a sole product. In desilylation of 15 with n-Bu_4NF, Payne rearrangement occurred to give two isomeric epoxy-alcohols(16a,b), acetylation of which afforded 17a and 17b, respectively. The same rearrangement was observed in the reaction of acetate(17a) with aq. K_2CO_3 in MeOH. Furthermore, 17b was converted to 18a by the treatment with phenyl selenide. Deselenylation of 18a in a usual manner afforded 19. Although attempts to construct a B ring by cyclization of 19 was fruitless, cyclization of 18a by N-hydroxy-methylation, followed by TFA treatment gave 22. Finally, 22 was treated with NalO_4 to give 23, whose ^1HNMR spectrum was identical with that of an authentic sample prepared for conversion to (±)-lycorine by Sano et al.
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 31 (0), 152-158, 1989
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
- 1390282681049481984
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- NII論文ID
- 110006678806
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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
