An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A.
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 N-O 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.
Gallos
John K
JK
Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 541 24, Greece. igallos@chem.auth.gr
Stathakis
Christos I
CI
Kotoulas
Stefanos S
SS
Koumbis
Alexandros E
AE
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013237:Stereoisomerism
D003517:Cyclopentanes; C008792:pentenomycin I; C031096:neplanocin A; D000241:Adenosine; C013905:cyclopentenone