Synthetic studies on d-biotin, part 9. An improved asymmetric synthetic route to d-biotin via Hoffmann-Roche lactone-thiolactone approach.
An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine-catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.
Chen
Fen-Er
FE
Department of Chemistry, Fudan University, Shanghai, People's Republic of China. rfchen@fudan.edu.cn
Jia
Hui-Qing
HQ
Chen
Xu-Xiang
XX
Dai
Hui-Fang
HF
Xie
Bin
B
Kuang
Yun-Yan
YY
Zhao
Jian-Feng
JF
D001710:Biotin / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D007783:Lactones; D013438:Sulfhydryl Compounds; D001710:Biotin