Ipso -Type Regiocontrolled Benzannulation for the Synthesis of Uniquely Substituted α-Arylnaphthalenes: Application to the First Total Synthesis of Chaihunaphthone.

ABSTRACT: A distinctive method for synthesizing a variety of multisubstituted α-arylnaphthalenes utilizing novel regiocontrolled ipso-type [4 + 2] benzannulation is presented. Ortho- and para-substituted 1-Ar¹-1-Ar²-2,2-dichlorocyclopropylmethanols (AACM) were transformed to the corresponding ipso-type α-arylnaphthalenes. (i) The reaction of ortho-AACM using TiCl₄ or SnCl₄ (1.0 equiv) proceeded smoothly to afford ipso-type α-arylnaphthalenes (seven examples; 49-69% yield) exclusively, without producing conventional benzannulation isomers. (ii) Para-AACM also underwent the reaction successfully to afford the desired ipso-type α-arylnaphthalenes (14 examples; 39-98% yield) without producing conventional

SUBMITTER: Moriguchi K 

PROVIDER: S-EPMC8296562 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature