46 STEREOCONTROLLED TOTAL SYNTHESIS OF PICROTOXANE SESQUITERPENOIDS, (-)-PICROTOXININ AND (+)-CORIAMYRTIN
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- Wakamatsu K.
- Faculty of Science, Nagoya University
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- Hida T.
- Faculty of Science, Nagoya University
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- Kigoshi H.
- Faculty of Science, Nagoya University
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- Niiyama K.
- Faculty of Science, Nagoya University
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- Yamada M.
- Faculty of Science, Nagoya University
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- Suzuki M.
- Faculty of Science, Nagoya University
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- Nagase H.
- Faculty of Science, Nagoya University
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- Niwa H.
- Faculty of Science, Nagoya University
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- Yamada K.
- Faculty of Science, Nagoya University
Bibliographic Information
- Other Title
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- 46 ピクロトキサン型セスキテルペノイド,(-)-ピクロトキシニンおよび(+)-コリアミルチンの全合成
Abstract
Stereocontrolled total synthesis of toxic sesquiterpenoids of picrotoxane type, (-)-picrotoxinin (1) and (+)-coriamyrtin (2) is described. The double cyclization of a conjugated cyclohexenone 4 afforded the isotwistane compounds, 10a and 10b, which were converted into properly functionalzed cis-hydrindane derivative 17 via novel bridgehead hydroxylation of the bicyclo[3.2.1]octan-2-one moiety in the isotwistane intermediate 5. Optical resolution of 17 was made and the resulting (+)-17 was converted into a common and key intermediate (-)-6, from which (-)-picrotoxinin (1) and (+)-coriamyrtin (2) were synthesized.
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 26 (0), 352-358, 1983
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390282681050808704
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- NII Article ID
- 110006678403
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed