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Enantioselective Total Synthesis of the Cyclophilin-Binding Immunosuppressive Agent Sanglifehrin A

✍ Scribed by Maosheng Duan; Leo A. Paquette

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 115 KB
Volume: 113
Category: Article
ISSN: 0044-8249
DOI: 10.1002/1521-3757(20011001)113:19<3744::aid-ange3744>3.0.co;2-b

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Scheme 1. Bismurrayaquinone A (1) and key biphenol 2. Scheme 2. a) PhI(OAc) 2 (1.2 equiv), MeOH, 91 %; b) Me 2 Zn (0.9 equiv), (S,R,R)-phosphoramidite ligand (4.5 mol %), Cu(OTf) 2 (2 mol %), 45-52 %; c) LDA (1.1 equiv); CuCl 2 (1.1 equiv), 63 %; d) BF 3 •OEt 2 (10 equiv), toluene, reflux, 87 %; e)