Review of Total Synthesis of Valienamine

Improved Stereoselective Syntheses of (+)‐Valiolamine and (+)‐Valienamine Starting from (–)‐Shikimic Acid

“…[14] Based on the above-mentioned biological and pharmaceutical importance, these two particular C 7 N aminocyclitols have attracted much interest from synthetic chemists. [1,15] Some elegant stereoselective total syntheses of ( ＋ )-valiolamine 1 and (＋)-valienamine 2 have been reported (Figure 2), these total syntheses have started from natural materials such as D-arabinose, [16] D-xylose, [17] D-glucose, [18,19] Dmannose, [20] D-or L-tartaric acid, [21,22] myo-inositol [(-)-vibo-quercitol], [23,24] ()-quinic acid [25,26] and quebrachitol, [27] or from unnatural materials such as Garner's aldehyde [28] and cyclohexadiene intermediates which could be obtained from the asymmetric Diels-Alder reaction. [29] (-)-Shikimic acid (Figure 1) is a naturally abundant and commercially available chiral compound, and it can be produced in large amount by extraction from Chinese star anise or other plants.…”