Divergent Synthesis and Biological Evaluation of 2,6-Disubstituted Tetrahydropyran-Containing Natural Products: Parvistone E, Goniothalesdiol A, 6-epi-Goniothalesdiol A, and 8-epi-9-Deoxygoniopypyrone

Abstract The concise and efficient synthesis of (+)-goniothalesdiol A and (–)-parvistone E (leiocarpin A), as well as the first total syntheses of (–)-6-epi-goniothalesdiol A and (–)-8-epi-9-deoxygoniopypyrone acetate, have been achieved in four or five longest linear steps based on the chiron approach. The potential biological activities of four 2,6-disubstituted tetrahydropyran-containing natural products were explored based on a panel of human cancer cell lines, BV-2 microglia and 3T3-L1 preadipocytes. Our results indicate that these four natural products display significant adipogenic activity in 3T3-L1 preadipocytes, but do not have clear effects on cancer cell proliferation or LPS stimulated microglia activation.