4 3-Sulfoleneを利用する共役ジエン類の新しい立体選択的合成法 : その天然有機化合物合成への応用(口頭発表の部)
書誌事項
- タイトル別名
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- 4 New stereoselective method for synthesizing conjugated dienes using 3-sulfolene as a masked diene synthon : Application to the syntheses of organic natural products
- 公開日
- 1987
- DOI
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- 10.24496/tennenyuki.29.0_25
- 公開者
- 天然有機化合物討論会実行委員会
説明
Reaction of 3-sulfolenes with various electrophiles in combination with stereoselective desulfonylation provided a new method for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes with exceedingly high stereoselectivity. 3-Sulfolenes (1) react with primary alkyl iodides, aldehydes, ketones, and α,β-unsaturated ketones to give the corresponding α-substituted 3-sulfolenes. The substituents on the 3-sulfolene ring exhibit remarkable effect on the regioselectivity of the reaction with electrophiles. Electron donating groups on the double bond effect selective substitution at the 2-position, while electron withdrawing groups cause substitution at the 5-position. When one of the α-position of the sulfolene is occupied by an alkyl group, electrophiles are exclusively introduced to the other α-position. A new method is developed for desulfonylating trans-2,5-substituted 3-sulfolenes (4) exclusively to (E,E)-conjugated dienes (10). The method is applied to the highly stereoselective syntheses of three insect pheromones having conjugated diene structure and monoterpene (E)-tagetone (17). Convenient methods for synthesizing hydrindane derivatives are developed by utilizing the diene synthesis in combination with intramolecular Diels-Alder reaction. The method is applied to the completely stereoselective synthesis of coronafacic acid (22), and asymmetric synthesis of the CD-ring and C(20)-C(22) part of vitamin D (26).
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 29 (0), 25-32, 1987
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
- 1390282681050057728
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- NII論文ID
- 110006678616
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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
