Pd(II)-mediated cyclodehydrogenation of formyldiarylamines-total synthesis of natural carbazoles clauraila A, clausenal and 6-methoxymurrayanine

Author(s)

Fumagalli, Fernando ^[1] ; Emery, Flavio da Silva ^[1]

Affiliation

^[1] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, Dept Pharmaceut Sci, BR-14040903 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron Letters; v. 56, n. 18, p. 2307-2310, APR 29 2015.
• Web of Science Citations: 9

Abstract

Using palladium(II)-catalyzed intramolecular C-H activation/C-C cross coupling we synthesized three natural carbazoles (clauraila A, clausenal, and 6-methoxymurrayanine) from formyldiarylamines. The versatile strategy used here allowed us to obtain these alkaloids with fewer synthetic steps and in similar overall yields to methods previously reported. We present the first use of Pd(acac)(2) as a catalyst for this cyclodehydrogenation, which is a novelty that reveals mechanistic details about the reaction. (C) 2015 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 12/20990-2 - Antiinfective compounds: an evolution in the medicinal chemistry of leishmanicidal tiazoles and the search for new tuberculostic agents
• Grantee: Flavio da Silva Emery
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/00727-8 - Medicinal Chemistry of Carbazole Alkaloids: Synthesis of claurailas and analogs targeting new antileishmanial compounds
• Grantee: Fernando Fumagalli
• Support Opportunities: Scholarships in Brazil - Master