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Synthesis of (+)‐Centrolobine and Its Analogues by Using Acyl Anion Chemistry
Author(s) -
Sudarshan Kasireddy,
Aidhen Indrapal Singh
Publication year - 2013
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.201300097
Subject(s) - chemistry , tetrahydropyran , stereoselectivity , ring (chemistry) , aryl , combinatorial chemistry , ion , organic chemistry , stereochemistry , catalysis , alkyl
A new route based on the use of acyl anion chemistry was developed for the synthesis of (+)‐centrolobine and its analogues. Acid‐catalyzed benzylic cation initiated cyclization was the key step in the stereoselective formation of the cis ‐2,6‐disubstituted tetrahydropyran ring. The developed methodology was applied to the synthesis of (+)‐centrolobine analogues containing electron‐donating substituents in the aryl rings.