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Total Synthesis of Unsymmetrical Benzils, Scandione and Calophione A
Author(s) -
Worayuthakarn Rattana,
Boonyaudtayan Sasiwadee,
Ruchirawat Somsak,
Thasaopporn
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301722
Subject(s) - chemistry , carbanion , benzofuran , total synthesis , palladium , intramolecular force , medicinal chemistry , ether , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
The synthesis of the title unsymmetrical benzils, scandione and calophione A, is described. The key processes involve intramolecular cyclization reaction of the carbanion at the benzylic position of the arylbenzyl ether to the adjacent ester group followed by oxidation. The palladium(II)‐catalyzed oxidative cyclization was also used to establish the benzofuran unit of calophione A.