The syntheses of (±)-PGEi and (±)-ll-deoxyprostaglandins in the E: and Fi series have been carried out by conjugate addition of bis(triethyl phosphite)copper(I) cyanide vinyllithium to the substituted cyclopentenones la and lb, and subsequent elaboration of vinylamylcarbinol side chain via the intermediate carboxaldehydes 3b and 3d. The intermediate 3d was also converted to (±)-9-oxo-13-czs-prostenoic acid (6c). These transformations are characterized by high yields and ease of operation. The synthesis of prostaglandins has been the subject of considerable synthetic effort during the past several years. In the course of this work a number of elegant syntheses of prostaglandins have been developed, but, in general, these approaches are lengthy and rather complex in nature.2
An
efficient, divergent, and straightforward access to novel C-glycosides has been developed, namely, α-hydroxy
carboxamide and carboxylic acid derivatives, via a green and scalable
process from unprotected carbohydrates. The method involves condensation
of 1,3-dimethylbarbituric acid with unprotected sugars followed by
subsequent barbiturate oxidative cleavage in the same pot. Further
expanding of the chemistry led to the development of efficient entries
to diastereoisomerically pure C-glycosyl-α-hydroxy
esters or amides through nucleophilic attack on a readily available
and versatile key lactone intermediate.
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