174657-20-6Relevant academic research and scientific papers
Total synthesis of bafilomycin A1
Toshima,Jyojima,Yamaguchi,Noguchi,Yoshida,Murase,Nakata,Matsumura
, p. 3271 - 3284 (2007/10/03)
The highly stereoselective total synthesis of the macrolide antibiotic, bafilomycin A1 (1), the first specific potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 16-membered tetraenic lactone and β-hydroxyl hemiacetal side-chain subunits. The C1-C17 16-membered lactone aldehyde 2 was synthesized through the coupling of the C5-C11 vinyl iodide 4 and the C12-C17 vinylstannane 5, followed by construction of the C1-C4 diene and macrolactonization. The aldol coupling of 2 and the C18-C25 ethyl ketone 3 followed by desilylation provided 1, which was identical with natural bafilomycin A1. The key synthetic segments 3-5 were effectively synthesized from the readily available chiral materials, D-glucose, ethyl (S)-lactate, and methyl (S)-3-hydroxy-2-methylpropionate, respectively.
Total synthesis of bafilomycin A1. 2. The assemblage and completion of the synthesis
Toshima, Kazunobu,Yamaguchi, Hiroyuki,Jyojima, Takaaki,Noguchi, Yasunobu,Nakata, Masaya,Matsumura, Shuichi
, p. 1073 - 1076 (2007/10/03)
The total synthesis of the macrolide antibiotic, bafilomycin A1 (1), has been achieved by a convergent route involving aldol condensation between the 16-membered lactonic aldehyde 2 and the ethyl ketone 3, followed by desilylation.
