Enantioselective syntheses of (R)- and (S)-argentilactone and their cytotoxic activities against cancer cell lines

Angelo de Fatima; Luciana Konecny Kohn; Márcia Aparecida Antônio; João Ernesto de Carvalho; Ronaldo Aloise Pilli

doi:10.1016/j.bmc.2004.07.044

Enantioselective syntheses of (R)- and (S)-argentilactone and their cytotoxic activities against cancer cell lines

Bioorg Med Chem. 2004 Oct 15;12(20):5437-42. doi: 10.1016/j.bmc.2004.07.044.

Authors

Angelo de Fatima¹, Luciana Konecny Kohn, Márcia Aparecida Antônio, João Ernesto de Carvalho, Ronaldo Aloise Pilli

Affiliation

¹ Instituto de Quimica, Unicamp, CP 6154, 13084-971, Campinas, São Paulo, Brazil.

PMID: 15388170
DOI: 10.1016/j.bmc.2004.07.044

Abstract

Concise total syntheses of (R)- and (S)-argentilactone have been developed via enantioselective catalytic allylation (ECA) and ring-closing metathesis pathways (four steps, 39% overall yield and 82-84% ee) from 2-octynal and their in vitro activity against cancer cells is described.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / toxicity*
Cell Line, Tumor
Female
Humans
Lactones / chemical synthesis*
Lactones / chemistry
Lactones / toxicity*
Male
Stereoisomerism

Substances

Antineoplastic Agents
Lactones
argentilactone