FeCl3 Catalyzed Synthesis of cis-Fused Reduced THC Analogues
Lucía Gurgone
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorTonino G. Adessi
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorAgustina La-Venia
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorCorresponding Author
Vincent Gandon
Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS 8182), Paris-Saclay University, bâtiment Henri Moissan, 17 avenue des sciences, 91400 Orsay, France
Search for more papers by this authorCorresponding Author
Martín J. Riveira
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorLucía Gurgone
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorTonino G. Adessi
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorAgustina La-Venia
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorCorresponding Author
Vincent Gandon
Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS 8182), Paris-Saclay University, bâtiment Henri Moissan, 17 avenue des sciences, 91400 Orsay, France
Search for more papers by this authorCorresponding Author
Martín J. Riveira
Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK Rosario, Argentina
Search for more papers by this authorGraphical Abstract
FeCl3 catalyzes the isomerization of 2-prenylated-2H-pyrans towards cis-fused tetrahydro-6H-benzo[c]chromene systems (cis-THC analogues). The same catalyst promotes the formation of these products via cyclocondensation of 1,3-dicarbonyl substrates and citral/farnesal-type aldehydes. The synthetic strategy could be applied to the racemic preparation of biologically relevant natural products cis-perrottetinene and Δ9-cis-tetrahydrocannabiorcol.
Abstract
Studies on a cycloisomerization reaction of 2-prenylated-2H-pyrans towards cis-fused tetrahydro-6H-benzo[c]chromene systems (reduced cis-THC analogues) are reported. The transformation is catalyzed by iron chloride and proceeds with the formation of two new bonds and two stereocenters diastereoselectively. The same catalyst also promotes the formation of these products via a one-pot tandem Knoevenagel condensation of 1,3-cyclohexanediones and citral or farnesal aldehydes, followed by cycloisomerization establishing a direct assembly of this important scaffold.
Conflict of Interests
The authors declare no competing financial interest.
Open Research
Data Availability Statement
The data underlying this study are available in the published article and its online supplementary material.
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