Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H

DELLA-FELICE, F.; SAROTTI, A.M.; PILLI, R.A.*

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2017 vol. 82 p. 9191 - 9197

0022-3263

The total synthesis and structural revision of (+)-cryptoconcatone H is 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, CM reaction and THP formation via Pd(II)-catalyzed cyclization. Finally, Krische allylation reaction established the last stereocenter and the lactone moiety was formed by RCM.