書誌事項
- タイトル別名
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- Rearrangement approaches to fused-polycyclic natural products from bicyclo[3.2.2]nonane derivatives.
- ビシクロ 3.2.2 ノナンルイ ノ テンイ ハンノウ オ カツヨウシタ シュ
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Bicyclo [3. 2. 2] nonane derivatives are prepared from tropones by Diels-Alder reaction with ethylene and from bicyclo [2. 2. 2] oct-5-en-2-ones by Tiffeneau-Demjanov ring enlargements. The methods developed for the construction of [m-n] fused-ring skeletons are the photochemical [3, 3] -sigmatropic rearrangement of bicyclo [3. 2. 2] nona-3, 6-dien-2-ones into endo-7-bicyclo [4. 1.0] hept-2-enylketenes and the photochemical [1, 3] -acyl migration of bicyclo [3. 2. 2] non-6-en-2-ones into bicyclo [4. 3. 0] non-4-en-7-ones. The pinacoltype rearrangement of 1-methoxybicyclo [3. 2. 2] non-6-en-2-ols derived from the corresponding ketones by Grignard reactions has been developed in order to establish the formal bridgehead-substitution of these ketones and/or to exchange the saturated bridges each other. The natural products synthesized on the basis of these methods are the [3-6] fused-ring sesquiterpenes (±) -sesquicarene (27), (±) -sirenin (28), and (±) -isosesquicarene (37), the [5-6] fused-ring furano-sesquiterpenes (±) -pinguisone (59) and (±) -deoxopinguisone (60), the [6-7] fused-ring sesquiterpene (±) -widdrol (92), and the antitumor antibiotic polyketide (±) -ptilocaulin (96).
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 45 (7), 654-663, 1987
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
- 1390282680289299456
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- NII論文ID
- 130000931144
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 3144105
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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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- 使用不可