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Synthesis of 6‐Alkyl‐6 H ‐benzo[ c ]chromene Derivatives by Cyclization/Selective Ether Cleavage in One Pot: Total Synthesis of Cannabinol
Author(s) -
Norseeda Krissada,
Tummatorn Jumreang,
Krajangsri Suppachai,
Thongsornkleeb Charnsak,
Ruchirawat Somsak
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600095
Subject(s) - chemistry , cannabinol , total synthesis , ether , alkyl , yield (engineering) , ether cleavage , cleavage (geology) , natural product , organic chemistry , stereochemistry , williamson ether synthesis , biochemistry , materials science , receptor , cannabinoid , geotechnical engineering , fracture (geology) , metallurgy , engineering
A convenient synthesis of 6‐alkyl‐6 H ‐benzo[ c ]chromenes is demonstrated in a one‐pot manner. This method involved the cyclization/selective ether cleavage of 1‐(2′‐alkoxybiaryl‐2‐yl)alkanol derivatives by using PBr 3 in the presence of LiI to obtain the corresponding products in good to excellent yields. Moreover, we also applied this method as a key step in the total synthesis of the natural product cannabinol, which was completed in four steps in good overall yield.