Intramolecular Diels-Alder reactions of
o-quinodimethane intermediates provide an useful method for synthesis of polycyclic ring systems.
The generation of
o-quinodimethane intermediates on the basis of thermal ring opening of benzocyclobutene, cheletropic elimination of 1, 3-dihydrobenzothiophene dioxide and 1, 4-elimination of
o- (trimethylsilylmethyl) benzyltrimethylammonium halide, which have been conveniently utilized for the syntheses of a variety of polycycles, is described, focusing on preparations of the precursors for the generation of α-substituted
o-quinodimethanes and their cyclizations to steroidal frameworks.
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