An efficient synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol and 1,4-dideoxy-1,4-imino-D- and L-xylitol from chiral aziridines

作者：Choi Hwan Geun; Park Dong Sik; Lee Won Koo; Sim Taebo^*

来源：Tetrahedron Letters, 2013, 54(43): 5775-5777.

DOI：10.1016/j.tetlet.2013.08.040

• D-AB1/L-AB1
• D-DIX/L-DIX
• Natural product
• Efficient synthesis
• Chiral aziridines

A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-D- and L-arabinitol (D-AB1, 1 and L-AB1, 3) and 1,4-dideoxy-1,4-imino-D- and L-xylitol (D-DIX, 2 and L-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis.

• 出版日期2013-10-23