N-Acetylcolchinol Methyl Ether (a Natural Product); Suhailamine (a Phantom Natural Product)

Abstract

The reported characterization data for the allocolchicinoid alkaloid suhailamine, isolated from Colchicum decaisnei and known to have an erroneous structure, have been reanalyzed. This analysis has led to the current proposal that suhailamine has the same structure as N-acetylcolchinol methyl ether (NCME), an assertion that is supported by comparison with previously reported data for NCME. Suhailamine is therefore a phantom natural product, while NCME represents a naturally occurring allocolchicinoid rather than a purely synthetic entity.

Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy

“…1a ), which displays potent anticancer activity by inhibition of the tubulin polymerization. 21 Due to the modularity of our electrosynthesis, this approach could be beneficial for preparing diverse derivatives of NSC 51046 from 3-phenyl-1-(3′,4,5′-trimethoxy-[1,1′-biphenyl]-2-yl)prop-2-yn-1-one 1a. Under the standard electrooxidative reaction conditions, the sulfonylation product 3a was obtained in high yield.…”

Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives

“…Among them are allocolchicinoids (Figure ), in which the tropolone ring C has been changed to a benzene ring, namely, natural (−)-allocolchicine ( 2 ), synthetic (−)- N -acetylcolchinol ( 3 ), and its methyl ether (NCME, 4 ). The water-soluble phosphate prodrug ZD6126 − ( 5 ) has even reached phase II clinical trials; however, the trials had to be stopped due to cardiotoxicity at therapeutic doses. Despite some serious limitations of the established colchicine-derived compounds, such as systemic toxicity, low water solubility, and a resulting poor bioavailability, there is a continuing high interest in such compounds.…”

“…Chemical structures of (−)-allocolchicine ( 2 ), (−)- N -acetylcolchinol ( 3 ), (−)- N -acetylcolchinol methyl ether (NCME, 4 ), and ZD6126 ( 5 ). − …”

In(ONf)3-catalyzed 7-membered carbon-ring-forming annulation of heteroarylindoles with α,β-unsaturated carbonyl compounds

“…Biaryls fused with a 7-membered carbon ring 1 are significant structural motifs found in biologically active compounds and natural products 2 as well as functional materials. 3 Due probably to this, a lot of synthetic methods to access the structure have been reported so far.…”