Shi Cong, Liu Ruihua, Wang Zemin, Li Xiaowei, Qin Hongyun, Yuan Leifeng, Shan Wenlong, Zhuang Wenli, Li Xiangqian, Shi Dayong
State Key Laboratory of Microbial Technology, Shandong University, 72 Binhai Road, Qingdao, 266237 Shandong, P. R. China.
Laboratory of Marine Drugs and Biological Products, Pilot National Laboratory for Marine Science and Technology, 168 Weihai Road, Qingdao, 266237 Shandong, P. R. China.
Org Lett. 2024 Apr 19;26(15):2913-2917. doi: 10.1021/acs.orglett.4c00348. Epub 2024 Apr 3.
C-C σ-bond cleavage and reconstruction is a significant tool for structural modification in synthetic chemistry but it remains a formidable challenge to perform on unstrained skeletons. Herein, we describe a radical addition-enabled C-C σ-bond cleavage/reconstruction reaction of unstrained allyl ketones to access various functional indanones bearing a benzylic quaternary center. The synthetic utility of this method has been showcased by the first total synthesis of carexane L, an indanone-based natural product.
碳-碳σ键的断裂与重建是合成化学中进行结构修饰的重要手段，但在无张力骨架上实现这一过程仍然是一项艰巨的挑战。在此，我们报道了一种自由基加成促进的无张力烯丙基酮的碳-碳σ键断裂/重建反应，用于合成各种带有苄基季碳中心的官能化茚满酮。该方法的合成实用性已通过基于茚满酮的天然产物Carexane L的首次全合成得到了展示。
