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

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Author(s):	-Felice, Franco Della ; Sarotti, Ariel M. ; Pilli, Ronaldo A. Total Authors: 3
Document type:	Journal article
Source:	Journal of Organic Chemistry; v. 82, n. 17, p. 9191-9197, SEP 1 2017.
Web of Science Citations:	8
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. (AU)

FAPESP's process:	14/25474-8 - Synthesis and biological evualuation of Brevipolide A, Cryptomoskatone F1 and related compounds
Grantee:	Franco Della Felice
Support Opportunities:	Scholarships in Brazil - Doctorate (Direct)


FAPESP's process:	16/12541-4 - A biomimetic approach to the total synthesis of Stemona alkaloids
Grantee:	Ronaldo Aloise Pilli
Support Opportunities:	Regular Research Grants


FAPESP's process:	13/07607-8 - OCRC - Obesity and Comorbidities Research Center
Grantee:	Licio Augusto Velloso
Support Opportunities:	Research Grants - Research, Innovation and Dissemination Centers - RIDC