Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.
[reaction: see text] A synthetic approach to the novel bis-spiroacetal moiety of spirolides B and D is reported. The strategy hinges upon successive formation of the spirocenters at C15 and C18 by radical oxidative cyclization, followed by base-induced rearrangement of a C19-20 alpha-epoxide to introduce the C19 hydroxyl group.
Furkert
Daniel P
DP
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.
Brimble
Margaret A
MA
D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry*; D005609:Free Radicals; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000080:Acetals; D001685:Biological Factors; D005609:Free Radicals; D013141:Spiro Compounds; C467770:spirolide B; C467769:spirolide D