Asymmetric Synthesis of cis-5-(Aminomethyl)-3-(4-methoxy­phenyl)dihydrofuran-2(3H)-one

Abstract

The asymmetric synthesis of (3R,5S)-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one, as the most potent selective inactivator of monoamine B, was successfully achieved by applying a newly developed synthetic method toward the key γ-aminomethyl-γ-lactone via intramolecular aziridine ring opening in 63% overall yield from a commercial starting material.

Key words

asymmetric synthesis - γ-aminomethyl-γ-lactone - aziridines - ring opening

• References

• 1a Youdim MB. H, Riederer PF. Handb. Clin. Neurol. 2007; 84: 93
• 1b Riederer P, Laux G. Exp. Neurobiol. 2011; 20: 1
• 1c Youdim MB. H, Bakhle YS. Br. J. Pharmacol. 2006; 147: S287
• 2 Erdem SS, Özpınar GA, Boz Ü. J. Enzyme Inhib. Med. Chem. 2014; 29: 81
• 3 Lu X, Silverman RB. Bioorg. Med. Chem. 1998; 6: 1851
• 4 Yadav NN, Jeong H, Ha H.-J. ACS Omega 2017; 2: 7525
• 5a Dudev T, Lim C. J. Am. Chem. Soc. 1998; 120: 4450
• 5b Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
• 6a Han SM, Ma SH, Ha HJ, Lee WK. Tetrahedron 2008; 64: 11110
• 6b Hu XE. Tetrahedron 2004; 60: 2701
• 6c Stamm H. J. Prakt. Chem. 1999; 341: 319
• 7 Yadav NN, Choi J, Ha HJ. Org. Biomol. Chem. 2016; 14: 6426
• 8 Shiina I. Chem. Rev. 2007; 107: 239
• 9a Cravotto G, Demetri A, Nano GM, Palmisano G, Penoni A, Tagliapietra S. Eur. J. Org. Chem. 2003; 4438
• 9b Viola A, Ferranzzano L, Ancona S, Gentilucci L, Tolomelli A. Tetrahedron 2014; 70: 6781
• 10a Lee WK, Ha HJ. Aldrichimica Acta 2003; 36: 57
• 10b Ha H.-J, Jung J.-H, Lee WK. Asian J. Org. Chem. 2014; 3: 1020
• 11 Stankovic S, D’hooghe M, Catak S, Eum H, Waroquier M, Van Speybroeck V, De Kimpe N, Ha H.-J. Chem. Soc. Rev. 2012; 41: 643
• 12 Ding Z, Silverman RB. J. Med. Chem. 1992; 35: 885