An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

…, CI Stathakis, SS Kotoulas, AE Koumbis

Index: Gallos, John K.; Stathakis, Christos I.; Kotoulas, Stefanos S.; Koumbis, Alexandros E. Journal of Organic Chemistry, 2005 , vol. 70, # 17 p. 6884 - 6890

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Citation Number: 56

Abstract

An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4- enals and hex-5-en-ones-2 followed by NO bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.