312962-27-9Relevant academic research and scientific papers
Revision of the absolute configuration of salicylihalamide A through asymmetric total synthesis
Wu, Yusheng,Esser, Lothar,De Brabander, Jef K.
, p. 4308 - 4310 (2007/10/03)
A highly E-selective ring-closing metathesis is the key to building the macrocyclic salicylate core of (+)-salicylihalamide A (1). The synthesis results in a reassignment of the absolute configuration of natural (-)-salicylihalamide A (2), a structurally
Asymmetric synthesis of the fully functional macrolide core of salicylihalamide: remote control of olefin geometry during RCM.
Fuerstner,Thiel,Blanda
, p. 3731 - 3734 (2007/10/03)
A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta-keto esters 13 and 16 catalyzed by [(R)-BINAP.RuCl(2)](2).NEt(3) and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the latter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.
