软烯醇化贝克-文卡特拉曼重排促进了二铬酮和相关 2-取代色酮的全合成。
Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones.
机构信息
Chaire de recherche sur les agents anticancéreux d'origine naturelle, Laboratoire d'analyse et de séparation des essences végétales (LASEVE), Département des Sciences Fondamentales , Université du Québec à Chicoutimi , 555, boulevard de l'Université , Chicoutimi , Québec , G7H 2B1 , Canada.
INRS-Institut Armand-Frappier, Université du Québec , 531, boulevard des Prairies , Laval , Québec H7V 1B7 , Canada.
出版信息
Org Lett. 2018 Dec 7;20(23):7424-7428. doi: 10.1021/acs.orglett.8b03148. Epub 2018 Nov 29.
A seven-step total synthesis of the original scaffold of cytotoxic dirchromones involving an unprecedented soft-enolization Baker-Venkataraman rearrangement was designed. The methodology enabled access to naturally occurring dirchromone 1 (21% overall yield) at gram-scale, which was screened for cytotoxicity against 13 cancer cell lines. The scope of the soft-enolization Baker-Venkataraman rearrangement encompasses diversely substituted dirchromones, including flavonoids, 2-styrylchromones, and 2-phenylethylchromones.
设计了一种包含前所未有的软烯醇化贝克 - 文卡特拉曼重排的七步全合成原始支架的方法。该方法能够以克级规模获得天然存在的二色酮 1（总产率为 21%），并对其进行了针对 13 种癌细胞系的细胞毒性筛选。软烯醇化贝克 - 文卡特拉曼重排的范围包括各种取代的二色酮，包括黄酮类、2-苯乙烯基色酮和 2-苯乙基色酮。
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