書誌事項
- タイトル別名
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- Biomimetic Type Total Syntheses of Carotenoids via Regiocontrolled Oxirane-Ring Cleavage
- エポキシド ノ カイカン ホウコウ オ セイギョ シタ カロテノイド ノ biomimetic ナ ゼン ゴウセイ
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We achieved biomimetic type total syntheses of various carotenoids by using oxirane-ring cleavage as a key reaction. The fascinating point of this strategy is as follows; selective preparation of tetrasubstituted olefinic compounds, cyclopentyl ketones, or 3,6-epoxides could be attained by optimization of side chain lengths and the terminal functional groups at the C-6-position of 5,6-epoxides as a result of regioselective oxirane-ring cleavage and subsequent reactions. In particular, Lewis acid-treatment of epoxide carrying an acetoxypropyl group at C-6 preferably provided tetrasubstituted olefinic compound. On the other hand, Lewis acid or aminium salt-treatment of epoxides carrying an acetoxyethyl or a siloxymethyl group at C-6, and epoxy dienal preferentially afforded cyclopentyl ketones. Treatment of epoxy dienoate and epoxy dienonitrile, possessing a free hydroxy group at the C-3-position with aminium salt preferentially afforded 3,6-epoxides. These resulting compounds were successfully utilized for the total syntheses of crassostreaxanthin B, mytiloxanthin, capsanthin, capsorubin, cucurbitaxanthin A, and cycloviolaxanthin, respectively. Total syntheses of amarouciaxanthin A and B, salmoxanthin, and deepoxysalmoxanthin utilizing oxirane-ring cleavage are also described.
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 73 (2), 161-170, 2015
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
- 1390001205341345792
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- NII論文ID
- 130005129433
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 026084905
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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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