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- 西井 良典
- 信州大学繊維学部
書誌事項
- タイトル別名
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- Highly Stereoselective Construction and Chiral Transfer Ring-expansion of Highly Substituted Cyclopropanes
- タチカン シクロプロパン ノ コウリッタイ センタクテキ ゴウセイ ト フセイ デンパンカン カクダイ ハンノウ
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説明
Highly stereoselective synthesis of multi-substituted cyclopropane is important owing to their distribution in nature, and significant biological activities of their analogs. We report here the highly stereoselective synthesis of multi-functionalized cyclopropanes using the SmI2-promoted Reformatsky-type reaction, acylation, silylation of 1-chlorocyclopropanecarboxylic esters, and the fundamental Reformatsky reaction of 1-bromocyclopropanecarboxylic esters. As the stereo inductive transformation of synthesized highly substituted cyclopropanes, we describe Lewis acid-mediated ring-expansion of methyl (arylhydroxymethyl)-cyclopropanecarboxylates to afford 1,2-dihydronaphthalene-3-carboxylic acid esters. In addition, total syntheses of (+/−)-cyclogalgravin, its dicarboxyl analog, and three kinds of (+)-podophyllic aldehydes have been achieved. Key steps include highly stereoselective constructions of tetra-substituted cyclopropanes and the Lewis acid-mediated chiral transfer ring expansion with excellent level of stereoinductions.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 73 (7), 701-712, 2015
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680318263424
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- NII論文ID
- 130005093743
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 026606475
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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
- NDL
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- 使用不可