Sequential Five-Membered Ring Formation via Intramolecular Alkene Insertion and Intramolecular Allene Insertion to a .PI.-Allylpalladium Intermediate.
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- Doi Takayuki
- Tokyo Institute of Technology, Department of Applied Chemistry
Bibliographic Information
- Other Title
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- π‐アリルパラジウム中間体への分子内アルケン挿入および分子内アレン挿入を経る連続的5員環骨格構築の研究
- パイ アリルパラジウム チュウカンタイ エ ノ ブンシ ナイ アルケン ソウニュウ オヨビ ブンシ ナイ アレン ソウニュウ オ ヘル レンゾクテキ 5インカン コッカク コウチク ノ ケンキュウ
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Abstract
Palladium (0) -catalyzed tandem cyclization of 6-allyl-2, 7-octadienyl acetate 4 afforded the trans-fused bicyclo [3.3.0] octane 5 by intramolecular alkene insertion to a π-allylpalladium intermediate with 5-exo mode, followed by another intramolecular alkene insertion to the resulting σ-alkylpalladium intermediate. The reaction of 6, a methyl substituted derivative at the 7 position, also provided the novel trans-fused 7 and 8 whereas that of 11 which has dimethyl groups at the 2 and 7 position lead to 12 via 6-exo cyclization. Intramolecular reactions of the π-allylpalladium intermediates to allene moieties afforded two modes of cyclization (15→16 and 32→33). The former reaction was applied to a synthesis of isoiridomyrmecin (31). A domino cyclization of acyclic 41 was achieved via five and six consecutive carbon-carbon bond formations to successfully provide tricyclic 44 and tetracyclic 43.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 59 (12), 1190-1194, 2001
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
- 1390001205278961536
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- NII Article ID
- 10012285643
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 6002601
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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