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À propos de : Total Synthesis of (+)-Polyoxin J        

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  • Total Synthesis of (+)-Polyoxin J
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  • Stereoselective total synthesis of (+)-polyoxin J is described. The synthesis was achieved in aconvergent manner by coupling protected thymine polyoxin C (19) and 5-O-carbamoyl polyoxamicacid 27 and subsequent removal of the protecting groups. The key steps of the synthesis of protectedthymine polyoxin C involved the stereoselective electrophilic epoxidation of E-allyl alcohol 7 derivedfrom isopropylidene d-ribose derivative 5, followed by regioselective epoxide opening of 8 andconversion of resulting azido diol 9 to protected thymine polyoxin C (19). Protected polyoxamicacid 27 was synthesized stereoselectively by utilizing Sharpless epoxidation of tartrate-derivedallylic alcohol 20 followed by a regioselective epoxide ring opening with diisopropoxytitanium diazide.
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