Gold(i)-catalyzed tandem cyclization of cyclopropylidene-tethered propargylic alcohols: an approach to functionalized naphtho[2,3-c]pyrans. 2020

Jian Li, and Fang Yang, and Weiwei Hu, and Bo Ren, and Zi-Sheng Chen, and Kegong Ji
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, P. R. China. chenzsh@nwsuaf.edu.cn jikegong@nwsuaf.edu.cn and College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, China.

An unprecedented gold(i)-catalyzed cyclization of cyclopropylidene-tethered propargylic alcohols via a 6-endo-dig enyne cyclization followed by a ring-opening of cyclopropane and nucleophilic closure reaction to construct naphtho[2,3-c]pyrans was developed. This transformation represents a highly efficient method for the synthesis of polycyclic compounds in one-pot, and two new rings are formed in an atom economic manner.

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