First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
- Citation data:
Tetrahedron: Asymmetry, ISSN: 0957-4166, Vol: 28, Issue: 2, Page: 246-249
- Publication Year:
- Chemical Engineering; Chemistry
The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8- epi -parvistone A, have been accomplished from commercially available trans -cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6 S,7 S,8 S )-isogoniothalamin oxide.