312962-27-9Relevant academic research and scientific papers
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.
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
