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Abstract
This study explores the synthesis of cyclic cis-vicinal phenyl ethylenes from oxotriphenylhexanoates. The reaction is a BBr3-promoted cyclization of 1,6-ketoesters (1) to five-membered diketo compounds (2). The synthesis is interesting as it constitutes one of the few examples of modular stereoselective synthesis of structures with a cis-oriented vicinal diphenylethylene. The core structure of 2 can be smoothly derivatized, which makes it a promising synthetic building block for further stereoselective synthetic applications.
Highlights
Cyclic compounds possessing adjacent C(sp3)−aryl moieties are widely present in nature
While in most cases these compounds have a trans-vic-diphenylethylene moiety such as indanone[1−7] and reservatrol-based natural products,[8−19] the cis-vic-diphenylethylene motif has been explored less. These interesting substances still show biological activity, and representative examples include both pharmaceuticals[20] and natural products (Figure 1a).[21−34] For example, the rocaglates, rocaglamide, and silvestrol have received widespread attention as they have been investigated for therapeutic targets such as cancer[21,34,35] and recently viruses like the coronavirus,[36] the Ebola virus,[37] and the hepatitis E virus.[38]
The results showed lower reactivity compared to that of OTHOs substituted at aromatic ring 3 (Ar3)
Summary
Cyclic compounds possessing adjacent C(sp3)−aryl moieties are widely present in nature. While in most cases these compounds have a trans-vic-diphenylethylene moiety such as indanone[1−7] and reservatrol-based natural products,[8−19] the cis-vic-diphenylethylene motif has been explored less. These interesting substances still show biological activity, and representative examples include both pharmaceuticals[20] and natural products (Figure 1a).[21−34] For example, the rocaglates, rocaglamide, and silvestrol have received widespread attention as they have been investigated for therapeutic targets such as cancer[21,34,35] and recently viruses like the coronavirus,[36] the Ebola virus,[37] and the hepatitis E virus.[38] synthetic strategies leading to the formation the cis-vic-diphenylethylene are attractive. Used as a starting material in the Dieckmann condensation would ensure total control of the cis-vicdiphenylethylene buildup (Figure 1b)
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