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Synthesis of Salvinorin A Analogues as Opioid Receptor Probes

2006; American Chemical Society; Volume: 69; Issue: 6 Linguagem: Inglês

10.1021/np060094b

1520-6025

Kevin Tidgewell, Wayne W. Harding, Anthony Lozama, Howard Cobb, Kushal Shah, Pavitra Kannan, Christina M. Dersch, Damon A. Parrish, Jeffrey R. Deschamps, Richard B. Rothman, Thomas E. Prisinzano,

Chemical synthesis and alkaloids

Several neoclerodanes, such as salvinorin A (1) and herkinorin (3), have recently been shown to possess opioid receptor activity in vitro and in vivo. To explore the structure−affinity relationships of this interesting class of compounds, we have synthesized a series of analogues from 1 isolated from Salvia divinorum. Here, we report the semisynthesis of neoclerodane diterpenes and their structure−affinity relationships at opioid receptors. This work will allow the further development of novel opioid receptor ligands.