A Concise, Biomimetic Total Synthesis of Stephacidin A and Notoamide B

摘要

Marine organisms, particularly fungi, are abundant sources of biologically active natural products that possess complex and diverse ring systems. Prenylated indole alkaloids such as the paraherquamides and brevianamides are fungal metabolites whose synthesis and biogenetic origin have been extensively investigated. Recently, several other structurally related prenylated indole alkaloids have been discovered from marine environments. Stephacidin A (1) and B (2) were isolated from the fungal strain Aspergillus ochraceus WC76466 and were shown to exhibit potent in vitro cytotoxicity against various human tumor cell lines (Scheme 1). Stephacidin B (2) was found to be especially potent against testosterone-dependent prostate LNCaP cells (IC50=60 nM).