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

Autor(es)

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

Afiliação do(s) autor(es)

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

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron Letters; v. 56, n. 18, p. 2307-2310, APR 29 2015.
• Citações Web of Science: 9

Resumo

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)

• Processo FAPESP: 12/20990-2 - Agentes anti-infecciosos: uma evolução dos estudos químico-medicinais de naftotiazóis leishmanicidas e a busca de novos agentes tuberculostáticos
• Beneficiário: Flavio da Silva Emery
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/00727-8 - Química Medicinal de alcaloides carbazólicos: Síntese de claurailas e análogos visando novos compostos leishmanicidas
• Beneficiário: Fernando Fumagalli
• Modalidade de apoio: Bolsas no Brasil - Mestrado