Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Rie Fujita; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1038/s41598-021-03448-9

Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Sci Rep. 2021 Dec 15;11(1):24078. doi: 10.1038/s41598-021-03448-9.

Authors

Rie Fujita¹, Kengo Hanaya¹, Takeshi Sugai¹, Shuhei Higashibayashi²

Affiliations

¹ Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo, 105-8512, Japan.
² Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo, 105-8512, Japan. higashibayashi-sh@pha.keio.ac.jp.

Abstract

Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.

Publication types

Research Support, Non-U.S. Gov't