Total Synthesis of Polygalolide A by Intramolecular C-Glycosylation
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- Adachi Masaatsu
- Graduate School of Bioagricultural Sciences, Nagoya University
Bibliographic Information
- Other Title
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- 分子内<i>C</i>-グリコシル化反応を利用したPolygalolide Aの全合成
- 分子内C-グリコシル化反応を利用したPolygalolide Aの全合成
- ブンシ ナイ C-グリコシルカ ハンノウ オ リヨウ シタ Polygalolide A ノ ゼン ゴウセイ
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Abstract
Total synyhesis of polygalolide A, a secondary metabolite isolated from a Chinese medicinal plant, was achieved. In order to construct an oxabicyclo[3.2.1] core skeleton, we have developed an intramolecular Ferrier-type C-glycosylation of a glucal modified with siloxyfuran as an internal nucleophile. Although the conditions found in the model experiments did not undergo the C-glycosylation, further examination led us to find that combination of TMSOTf and 2,4,6-collidine was the best condition, giving oxabicyclo[3.2.1]octene with correct quaternary stereogenic centers in high yield. The successful production of the single diastereomer indicated that the siloxy group at the C-3 position played a crucial role for the stereocontrol. After transformation into tetracyclic intermediate, a phenolic moiety was finally introduced by Mukaiyama aldol reaction to furnish polygalolide A.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 73 (6), 607-615, 2015
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680318194176
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- NII Article ID
- 130005088786
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 026544907
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed