Synthesis of putative uniflorine A.
A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono-Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.
Davis
Andrew S
AS
Department of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Pyne
Stephen G
SG
Skelton
Brian W
BW
White
Allan H
AH
D000085:Acetates / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis*; D000478:Alkylation; D018360:Crystallography, X-Ray; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000085:Acetates; D000470:Alkaloids; D007212:Indolizines; C487671:uniflorine A