Rh(I)-catalyzed Cyclizations via Rhodacycle Intermediates: Application to the Synthesis of (.+-.)-Epiglobulol
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- Oonishi Yoshihiro
- Graduate School of Pharmaceutical Sciences, Hokkaido University
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- Mori Miwako
- 北海道医療大学
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- Sato Yoshihiro
- Graduate School of Pharmaceutical Sciences, Hokkaido University
Bibliographic Information
- Other Title
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- ローダサイクル中間体を経由する新規環化反応とその応用
- ローダ サイクル チュウカンタイ オ ケイユスル シンキ カンカ ハンノウ ト ソノ オウヨウ
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Abstract
Rh (I)-catalyzed hydroacylation of 4, 6-dienals proceeded smoothly, giving cycloheptenone derivatives. It was found that the size of the ring formed in this hydroacylation was dependent on the presence of a substituent at C 7 position and the geometry of the olefin. During ongoing investigation of this reaction, we found that Rh (I) -catalyzed cycloisomerization of 1, 3-dienes with alkenes in a tether gave cyclopentene derivatives in good yields. It was interesting that the existence of a heteroatom between a 1, 3-diene moiety and alkene in the tether affected the reaction course and that only a [4+2] cycloaddition product was produced. These two reactions proceeded using the same cationic Rh (I) catalyst under almost the same reaction conditions. We therefore investigated a new cascade reaction by a combination of these reactions. It was found that this reaction gave the bicyclo [5.3.0] decenone derivative in a stereoselective manner, and the Thorpe-Ingold effect played an important role in the second cycloisomerization step of this cascade cyclization. By the use of this cascade cyclization as a key step, the synthesis of (±) -epiglobulol has been accomplished.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 65 (3), 183-193, 2007
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
- 1390282680289726976
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- NII Article ID
- 10018578076
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD2sXjtFOjsLg%3D
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- ISSN
- 18836526
- 00379980
- http://id.crossref.org/issn/00379980
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- NDL BIB ID
- 8738176
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed