Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

…, SPJM Van Nispen, HA Boots, MW Tijhuis

Index: Ottenheijm, Harry C.J.; Liskamp, Rob M.J.; Nispen, Simon P.J.M. van; Boots, Hans A.; Tijhuis, Marian W. Journal of Organic Chemistry, 1981 , vol. 46, # 16 p. 3273 - 3283

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Citation Number: 63

Abstract

The total syntheses of sparsomycin (l), a naturally occurring antibiotic and antitumor substance, and its three stereomers 65-67 are described for the first time. In a convergent approach, the carboxylic acid 2 and the amine 3 were synthesized followed by amide formation (Scheme I). The acid 2 was prepared (23% yield) from 6-methyluracil (12) by coupling the aldehyde 19 with the phosphorane 20 (Scheme 111). The synthesis of the ...