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A Three‐Step Synthesis of the Guaianolide Ring System
Author(s) -
Hullaert Jan,
Laplace Duchan R.,
Winne Johan M.
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.201402170
Subject(s) - chemistry , cycloaddition , furan , ring (chemistry) , intramolecular force , stereoselectivity , trifluoromethanesulfonate , substrate (aquarium) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , oceanography , geology
By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan‐derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way.