Catalytic synthesis of Type II polyketides via Hydrogen-Mediated C-C bond formation

• Grant number: 17/00734-5
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• Start date: September 01, 2017
• End date: August 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Aparecido Sigoli
• Grantee: Gilmar Araujo Brito Junior
• Supervisor: Michael J. Krische
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: University of Texas at Austin (UT), United States
• Associated to the scholarship: 15/22426-5 - Synthesis of lanthanide complexes with potential applications as luminescent markers and asymmetric catalysts in organic synthesis, BP.PD

Abstract

The project in question refers to the synthesis of type II polyketides employing methodologies developed in the group of Prof. Krische. The research group of Prof. Krische has specialized in C-H functionalization of alcohols and unsaturated systems, mediated by organometallic osmium, ruthenium and iridium, generating coupled products with high complexity. Unlike traditional approaches to polyketides, direct alcohol C-C coupling bypasses use of chiral auxiliaries, premetallated C-nucleophiles, and discrete alcohol-to-aldehyde redox reactions. Alcohol C-C coupling will be employed in the synthesis of polyketide like (+)-lactonamycin and arenimycin. These syntheses symbolize strategies by which numerous bioactive type II polyketides may be prepared.

Scientific publications

(4)

(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)

SCHWARTZ, LEYAH A.; HOLMES, MICHAEL; BRITO, GILMAR A.; GONCALVES, THEO P.; RICHARDSON, JEFFERY; RUBLE, J. CRAIG; HUANG, KUO-WEI; KRISCHE, MICHAEL J.. Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters. Journal of the American Chemical Society, v. 141, n. 5, p. 2087-2096, FEB 6 2019. (17/00734-5)

BRITO, GILMAR A.; JUNG, WOO-OK; YOO, MINJIN; KRISCHE, MICHAEL J.. Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 58, n. 52, NOV 2019. (17/00734-5)

KIM, SEUNG WOOK; WURM, THOMAS; BRITO, GILMAR A.; JUNG, WOO-OK; ZBIEG, JASON R.; STIVALA, CRAIG E.; KRISCHE, MICHAEL J.. Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity. Journal of the American Chemical Society, v. 140, n. 29, p. 9087-9090, JUL 25 2018. (17/00734-5)

BRITO, GILMAR A.; DELLA-FELICE, FRANCO; LUO, GUOSHUN; BURNS, ALEXANDER S.; PILLI, RONALDO A.; RYCHNOVSKY, SCOTT D.; KRISCHE, MICHAEL J.. Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling. ORGANIC LETTERS, v. 20, n. 13, p. 4144-4147, JUL 6 2018. (17/00734-5, 17/18487-4)