Synthesis of the western half of the lolicines and lolitrems.
[reaction: see text] The synthesis of the highly substituted indole portion of the complex tremorgenic natural products lolicine A and B is presented. The Diels-Alder reaction of a quinone monoimine enables the synthesis of an appropriately substituted indole. The key step in the synthesis is a tandem isopropenyl cuprate addition/aldol cyclocondensation which provides the necessary functionality for elaboration to the 2,2,5,5-tetramethyltetrahydrofuran.
England
Dylan B
DB
Department of Chemistry, The University of Western Ontario, London, Canada.
Magolan
Jakob
J
Kerr
Michael A
MA
D018360:Crystallography, X-Ray; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D003904:Mitosporic Fungi / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D007211:Indoles; D009183:Mycotoxins; D013729:Terpenes; C518045:lolicine A; C518046:lolicine B