化学
非对映体
代谢物
立体化学
单体
联轴节(管道)
全合成
有机化学
生物化学
机械工程
工程类
聚合物
作者
Miho Kaneko,Zhenwu Li,Matthew T. Burk,Laureen Colis,Seth B. Herzon
摘要
(−)-Lomaiviticin A (1) is a genotoxic C2-symmetric metabolite that arises from the formal dimerization of two bis(glycosylated) diazotetrahydrobenzo[b]fluorenes. Here we present a synthesis of the monomer 17 and its coupling to form (2S,2′S)-lomaiviticin A (4), an unnatural diastereomer of 1. (2S,2′S)-Lomaiviticin A (4) is significantly less genotoxic, a result we attribute to changes in the orientation of the diazofluorene and carbohydrate residues, relative to 1. These data bring the importance of the configuration of the conjoining bond to light and place the total synthesis of 1 itself within reach.
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