書誌事項
- タイトル別名
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- Single-Step Construction of Deoxypropionate Motif by Stereospecific Propylene Oligomerization
- プロピレン ノ リッタイ トクイテキ オリゴマーカ ニ ヨル デオキシプロピオナート コウゾウ ノ タンダンカイ コウチク
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抄録
<p>In nature, many complex structures are assembled from simple molecules by a series of tailored enzyme-catalyzed reactions. One representative example is the deoxypropionate motif, an alternately methylated alkyl chain containing multiple stereogenic centers, which is biosynthesized by a series of enzymatic reactions from simple building blocks. In organic synthesis, however, the majority of the reported routes require the syntheses of complex building blocks. Furthermore, multistep reactions with individual purifications are required at each elongation. Here we show the construction of the deoxypropionate structure from propylene in a single step to achieve facile (formal) total syntheses of natural products containing syn or anti-deoxypropionate motif. To realize this strategy, we focused on the coordinative chain transfer polymerization and optimized the reaction condition to afford a stereo-controlled oligomer, which is contrastive to the other synthetic strategies developed to date that require 3-6 steps per unit, with unavoidable byproduct generation. Furthermore, multiple oligomers with different number of deoxypropionate units were isolated from one batch, showing application to the construction of library. Our strategy opens the door for facile synthetic routes toward other natural products that share the deoxypropionate motif.</p>
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 79 (2), 100-108, 2021-02-01
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
- 1390005667265739136
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- NII論文ID
- 130007983388
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 031265303
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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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