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Total Synthesis of (R)-Puraquinonic Acid using Enantiosselective C(sp3)-H Activation

Grant number: 16/22636-2
Support type:Scholarships abroad - Research
Effective date (Start): May 29, 2017
Effective date (End): May 28, 2018
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Marcus Vinicius Craveiro
Grantee:Marcus Vinicius Craveiro
Host: Olivier Baudoin
Home Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil
Research place: University of Basel, Switzerland  


This project proposes the asymmetric total synthesis of (R)-puraquinonic acid, a natural product that belongs to the class of illudalane sesquiterpenes. The key step consists of an intramolecular cyclization by enantioselective C(sp3)-H activation using organometallic catalysis. In this cyclization, there is the formation of an indane with a quarternary stereogenic center and the stereochemistry would be defined by using of chiral ligands.

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Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
MELOT, ROMAIN; CRAVEIRO, MARCUS V.; BAUDOIN, OLIVIER. Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp(3))-H Activation Strategy. Journal of Organic Chemistry, v. 84, n. 20, p. 12933-12945, . (16/22636-2)
MELOT, ROMAIN; CRAVEIRO, MARCUS V.; BURGI, THOMAS; BAUDOIN, OLIVIER. Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd-0-Catalyzed Asymmetric C(sp(3))-H Activation. ORGANIC LETTERS, v. 21, n. 3, p. 812-815, . (16/22636-2)

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