Palladium(0)-mediated desymmetrization of meso tetraols: an approach to the C3-C17 bis-oxane segment of phorboxazoles A and B.
[reaction: see text] meso-Tetraol bis(allylic acetates) 2 and 5 were synthesized via two-directional chain elongation. A palladium-mediated, ligand-controlled desymmetrization provided the desired bis-oxanes in greater than 98% ee. Bis-oxanes 1 and 4 represent potential synthetic intermediates for the C3-C17 subunits of phorboxazoles A and B.
Lucas
Brian S
BS
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
Burke
Steven D
SD
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A; D010165:Palladium