6-Endo-Trig Mode Cyclization to a Hydrindanone Using Samarium (II) Iodide
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- SONO Masakazu
- <i>Faculty of Pharmaceutical Sciences, Tokushima Bunri University</i>
Bibliographic Information
- Other Title
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- ヨウ化サマリウムを用いた6-Endo-Trig 型の環化反応によるヒドリンダノン類縁体の合成
- ヨウカ サマリウム オ モチイタ 6 Endo Trigガタ ノ カンカ ハンノウ ニ ヨル ヒドリンダノン ルイエンタイ ノ ゴウセイ
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Description
Samarium(II) iodide has been employed to promote the vinylogous pinacol coupling reaction of aldehyde to α, β-unsaturated ketones. The diastereoselectivity of 6-endo-trig mode products was changed by the addition of a proton source and/or HMPA and by the reaction temperature. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species, resulting in the cis-orientation in respect of the hydroxyl group at C-4 and the juncture proton at C-3a under mild reaction conditions. Coronafacic acid has been synthesized from a hydrindanone prepared by the cyclization reaction of the enone-aldehyde with samarium(II) iodide.<br>
Journal
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- YAKUGAKU ZASSHI
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YAKUGAKU ZASSHI 123 (8), 653-663, 2003-08-01
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001206127811200
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- NII Article ID
- 110003614914
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- NII Book ID
- AN00284903
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- COI
- 1:STN:280:DC%2BD3szpsFWnsw%3D%3D
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- ISSN
- 13475231
- 00316903
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- NDL BIB ID
- 6658456
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- PubMed
- 12931661
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed