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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.)

Total Synthesis of (+/-)-Brussonol and (+/-)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides

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Ahmad, Anees [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 2
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ORGANIC LETTERS; v. 21, n. 15, p. 6079-6083, AUG 2 2019.
Web of Science Citations: 1

The short and stereoselective syntheses of diterpenes (+/-)-brussonol and (+/-)-komaroviquinone, via a Ni-catalyzed epoxide ring-opening approach in the presence of aryl halides, is described. Key steps involve the effective preparation of a challenging hemiacetal intermediate in a single operation, followed by a highly efficient BF3 center dot OEt2-catalyzed Friedel-Craft alkylation, to construct the tricyclic skeleton of these diterpenes. The synthetic approach might offer a unified route for the synthesis of several natural products containing icetexane motifs. (AU)

FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
Grantee:Carlos Alberto Montanari
Support type: Research Projects - Thematic Grants
FAPESP's process: 15/20084-0 - Total synthesis of (-)-Brussonol, (+)-Komaroviquinona and its analogs targeting potential candidates with trypanocidal activity
Grantee:Anees Ahmad
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass
Grantee:Antonio Carlos Bender Burtoloso
Support type: Regular Research Grants