197723-40-3Relevant academic research and scientific papers
Total synthesis of vancomycin - Part 1: Design and development of methodology
Nicolaou,Li, Hui,Boddy, Christopher N. C.,Ramanjulu, Joshi M.,Yue, Tai-Yuen,Natarajan, Swaminathan,Chu, Xin-Jie,Braese, Stefan,Ruebsam, Frank
, p. 2584 - 2601 (2007/10/03)
o-Halosubstituted aromatic triazenes (e.g. I, Scheme 1) react with aryloxides (e.g. II, Scheme 1) in the presence of CuBr · Me2S, K2CO3 and pyridine in acetonitrile at reflux to afford biaryl ethers (e.g. V, Scheme 1). This general methodology (Tables 1 and 2) was applied to the construction of the C-O-D and D-O-E vancomycin model systems 37 (Scheme 2) and 50 (Scheme 3), demonstrating its potential in a projected total synthesis of vancomycin (1. Figure 1). For the construction of the vancomycin model AB biaryl ring system, a sequential strategy involving a Suzuki coupling of the C-O-D aryl iodide 74 (Scheme 7) and boronic acid 53 (Scheme 4), followed by macrolactamization was demonstrated, in which the preformed C-O-D ring framework served to preorganize the precursor for cyclization. The latter investigation led to Suzuki-coupling-based asymmetric synthesis of biaryl systems in which 2,2-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was found to be the optimum ligand (Tables 3 and 4).
A Suzuki coupling-macrolactamization approach to the AB-COD bicyclic system of vancomycin
Nicolaou,Ramanjulu,Ramanjulu, Joshi M.,Natarajan,Natarajan, Swaminathan,Brase,Braese, Stefan,Li,Li, Hui,Boddy,Boddy, Christopher N. C.,Rubsam,Ruebsam, Frank
, p. 1899 - 1900 (2007/10/03)
The effectiveness of the Suzuki coupling reaction in the formation of the AB biaryl moiety and the beneficial role of a preexisting COD ring system in a lactamization approach to the AB-COD ring system of vancomycin is demonstrated.
