カルボニルーエン反応を鍵反応としたビシクロ[3.3.1]ノナン骨格の構築と天然物合成への応用
書誌事項
- タイトル別名
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- Construction of bicyclo[3.3.1]nonane ring system by means of an intramolecular carbonyl-ene reaction, and its application to the synthesis of related natural products
抄録
(+)-Upial, isolated from the Kaneohe Bay, Oahu sponge Dysidea fragilis, was found to be a nonisoprenoid sesquiterpene aldehyde lactone containing the rare bicyclo[3.3.l]nonane skeleton. Due to its architecturally intriguing structural feature, upial and related analogues have received considerable attention from synthetic chemists over the years. The crucial step for the synthesis of upial lies in the stereocontrolled construction of a bicyclo[3.3.1]nonane ring system with five asymmetric carbon centers as well as facile introduction of the exo-methylene unit. To achieve this crucial step, we planned to exploit an intramolecular carbonyl-ene reaction of a corresponding allylsilane derivative, and we could establish a concise total synthesis of (+)-upial. This synthesis afforded the target compound in 10.2% overall yield in 15 steps from the readily accessible known starting material. Application of the strategy to the synthesis of trifarienols A and B was also investigated.
収録刊行物
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- 反応と合成の進歩シンポジウム 発表要旨概要
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反応と合成の進歩シンポジウム 発表要旨概要 34 (0), 137-137, 2008
日本薬学会化学系薬学部会
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- CRID
- 1390282680612896512
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- NII論文ID
- 130006998857
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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
- CiNii Articles
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- 使用不可