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Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
Fecha
2017-09Registro en:
Della Felice, Franco; Sarotti, Ariel Marcelo; Pilli, Ronaldo A.; Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H; American Chemical Society; Journal of Organic Chemistry; 82; 17; 9-2017; 9191-9197
0022-3263
CONICET Digital
CONICET
Autor
Della Felice, Franco
Sarotti, Ariel Marcelo
Pilli, Ronaldo A.
Resumen
The total synthesis and structural revision of (+)-cryptoconcatone H are described. Guided by computational studies for the final structure assignment, the stereogenic centers at the tetrahydropyran moiety of (+)-cryptoconcatone H were assembled through catalytic asymmetric methodologies: Krische allylation, cross-metathesis reaction, and THP formation via Pd(II)-catalyzed cyclization. Finally, a Krische allylation reaction established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.