Access to [6-7-6]-Icetexanes through Sequential Cascade Cyclization and Biomimetic Ring Expansion

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초록

We herein report an efficient synthetic method for preparing [6-7-6]-icetexane derivatives. This approach employs our previously designed copper-catalyzed intramolecular cyclization of enyne-aryl carbonyl substrates to generate a [6-6-6]-tricyclic abietane framework and a subsequent ring expansion protocol for the [6-7-6] scaffold. By synergizing these protocols, we established a highly efficient pathway for synthesizing icetexane compounds from readily available enyne-aryl starting materials, exhibiting remarkable versatility in accommodating various functional groups while delivering consistently high yields.

키워드

biomimetic reaction; carbocation rearrangement; copper; cyclization; ring expansion; BIOLOGICAL-ACTIVITY; DITERPENOIDS; (+/-)-BRUSSONOL
제목
Access to [6-7-6]-Icetexanes through Sequential Cascade Cyclization and Biomimetic Ring Expansion
저자
Le, Thuy Quynh; Liaba, Niaz; Jeong, Da In; Lee, Jeonghyo; Oh, Chang Ho
DOI
10.1002/ajoc.202300545
발행일
2024-01
유형
Article; Early Access
저널명
Asian Journal of Organic Chemistry
권
13
호
1
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