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

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

Abstract

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.

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, OCT 18 2019. (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, FEB 1 2019. (16/22636-2)

LONGO, JR., LUIZ S.; CRAVEIRO, MARCUS V.. Deep Eutectic Solvents as Unconventional Media for Multicomponent Reactions. Journal of the Brazilian Chemical Society, v. 29, n. 10, p. 1999-2025, OCT 2018. (16/22636-2, 07/07338-6, 15/11155-0)