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Regio‐ and Stereoselective Synthesis of Rotationally Hindered C 12 ‐Naphthylated Tribenzo[ a,c,j ]xanthenes through Catalytic Tricyclization of Yne‐Allenones
Author(s) -
Zhu ShanShan,
Li Heng,
Fu Rong,
Hao WenJuan,
Wang ShuLiang,
Tu ShuJiang,
Jiang Bo
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100061
Subject(s) - chemistry , stereoselectivity , annulation , catalysis , triple bond , cascade , stereochemistry , cycloaddition , bond cleavage , lewis acids and bases , combinatorial chemistry , medicinal chemistry , organic chemistry , double bond , chromatography
A Lewis acid‐catalyzed tricyclization of yne‐allenones with 1‐alkynylnaphthalen‐2‐ols has been developed, and used to produce a wide range of rotationally hindered tribenzo[ a,c,j ]xanthenes with generally good yields and stereoselectivity. This process involves a complex [2+2] cycloaddition relay and [4+2] cyclization cascade, enabling scission/recombination of C−C triple bonds to access unprecedented hexaheterocyclic architectures. The reaction also features good compatibility with different types of substituents, triple annulation cascade and the efficient control of regio‐ and stereochemistry.