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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Enantioselective Total Synthesis of (+)-Lyngbyabellin M

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Pirovani, Rodrigo V. [1] ; Brito, Gilmar A. [1] ; Barcelos, Rosimeire C. [1] ; Pilli, Ronaldo A. [1]
Total Authors: 4
[1] Univ Campinas UNICAMP, Inst Chem, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: MARINE DRUGS; v. 13, n. 6, p. 3309-3324, JUN 2015.
Web of Science Citations: 6

Lyngbyabellin M is a non-ribosomal peptide synthetase/polyketide synthase derived metabolite isolated from the cyanobacterium M. bouillonii displaying thiazole rings and a distinct chlorinated octanoic acid chain. Its absolute configuration was proposed based on the comparison of its spectroscopic data with those of other representatives of this family of marine natural products, as well as degradation and derivatization studies. Here the first total synthesis of (+)-lyngbyabellin M is described based on the coupling of three key intermediates: two chiral thiazole moieties and an anti hydroxycarboxylic acid prepared stereoselectively via a boron enolate mediated aldol reaction directed by Masamune's chiral auxiliary. (AU)

FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
Grantee:Ronaldo Aloise Pilli
Support type: Research Projects - Thematic Grants
FAPESP's process: 10/00336-0 - Artificial Nucleases Derived from Beta-carboline Alkaloids. Synthesis, Phosphodiester Recognition and Catalytic Activity.
Grantee:Rodrigo Vezula Pirovani
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 10/00219-4 - Asymmetric synthesis and structural determination of (-)-parviestemoamide.
Grantee:Gilmar Araujo Brito Junior
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 13/07607-8 - OCRC - Obesity and Comorbidities Research Center
Grantee:Licio Augusto Velloso
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC