Tetrahedron

Simple approach to O-protected deaminotunicaminyluracil

W Karpiesiuk, A Banaszek

Index: Karpiesiuk, Wojciech; Banaszek, Anna Tetrahedron, 1994 , vol. 50, # 9 p. 2965 - 2974

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Citation Number: 14

Abstract

A five-step synthesis of deaminotunicaminyluracil is presented. Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield. The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6. For this purpose several hydroborating reagents were examined. The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product. ...