Synthesis of Putative Uniflorine A

• Published in: Journal of organic chemistry Vol. 69; no. 9; pp. 3139 - 3143
• Main Authors: Davis, Andrew S, Pyne, Stephen G, Skelton, Brian W, White, Allan H
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 30.04.2004; Amer Chemical Soc
• Subjects: Acetates - chemistry; Alkaloids - chemical synthesis; Alkylation; Chemistry; Chemistry, Organic; Crystallography, X-Ray; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Indolizines - chemical synthesis; Magnetic Resonance Spectroscopy; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; RUTHENIUM ALLENYLIDENE COMPLEXES; ASYMMETRIC-SYNTHESIS; RING-CLOSING METATHESIS; ENANTIOSELECTIVE SYNTHESIS; AZASUGARS; INDOLIZIDINE ALKALOIDS; (+)-1,2-DI-EPI-SWAINSONINE; OLEFIN METATHESIS; CASTANOSPERMINE; N-BOC-2-ACYL OXAZOLIDINE METHODOLOGY; Indolizine derivatives; Nitrogen heterocycle; Metathesis; Natural product; NMR spectrometry; X ray diffraction; Diastereoselectivity; Xylose; Alkaloid; Cyclization; Mannich reaction; Polyol; Chemical synthesis; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo049806y

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.