An efficient synthesis of the polar part of sulfamisterin and its analogs

作者：Martinkova Miroslava^*; Gonda Jozef; Uhrikova Alena; Raschmanova Jana Spakova; Kuchar Juraj

来源：Carbohydrate Research, 2012, 352: 23-36.

DOI：10.1016/j.carres.2012.02.019

• Sulfamisterin
• Mycestericins
• Aza-Claisen rearrangement
• Isothiocyanates
• Trichloroacetamides
• Microwave irradiation

An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs.

• 出版日期2012-5-1