Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H
Franco Della-Felice1, Ariel M Sarotti2, Ronaldo A Pilli1
1University of Campinas , Institute of Chemistry, 13084-971 Campinas, SP, Brazil.
Abstract:
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.
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