Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies

Author(s)

Novaes, Luiz F. T. ^[1] ; Goncalves, Kaliandra de Almeida ^[2] ; Trivella, Daniela B. B. ^[2] ; Pastre, Julio C. ^[1]

Affiliation

^[1] Univ Estadual Campinas, UNICAMP, Inst Chem, POB 6154, BR-13084971 Campinas, SP - Brazil

^[2] Natl Ctr Res Energy & Mat, Brazilian Biosci Natl Lab, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 83, n. 9, p. 5160-5176, MAY 4 2018.
• Web of Science Citations: 3

Abstract

This article describes our efforts toward the total synthesis of actinoranone. Our synthesis strategies rely on a convergent route to connect the terpenoid and polyketide fragments, employing catalysis and powerful classical reactions for the assembly of these key fragments. A new transformation was disclosed during this work, a domino ring-opening and esterification. Initial cytotoxic studies for the selected synthesis intermediates are also presented. (AU)

• FAPESP's process: 15/08199-6 - Application of Dioxiranes in continuous flow, synthesis of Actinoranone and decalin fragment of Azadirachtin
• Grantee: Luiz Fernando Toneto Novaes
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Research Grants - Young Investigators Grants