Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: synthesis and structure elucidation of capensifuranone.
The synthesis of capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arrays. The assignment of relative and absolute stereochemistry of 1 has been made following the high-field NMR characterizations of synthetic diol derivatives. The previously unassigned C4 stereochemistry of 1 was determined to be of the (S)-configuration. The thermodynamic equilibration of capensifuranone and its C4 diastereomer has been examined.
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, USA. williamd@indiana.edu
David R
DR
Williams
Andrea L
AL
Nold
Richard J
RJ
Mullins
D000818:Animals; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D001685:Biological Factors; D005663:Furans; D007202:Indicators and Reagents; C488882:capensifuranone