First approach to the frondosin C ring system via a tandem cyclization/Claisen rearrangement sequence.
[reaction: see text] A one-pot tandem 5-exo cyclization/Claisen rearrangement strategy is utilized as the key step in the straightforward construction of the tetracyclic ring system of frondosin C. This reaction is done under microwave irradiation in the presence of catalytic MeLi.
Martínez
Isamir
I
Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA.
Alford
Philip E
PE
Ovaska
Timo V
TV
D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure
D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; C506349:frondosin C