A concise sultone route to highly oxygenated 1,10-seco-eudesmanolides - Enantioselective total synthesis of the antileukemic sesquiterpene lactones (-)-eriolanin and (-)-eriolangin

摘要

Using a sultone as the key intermediate, the first enantioselective total synthesis of the antileukernic 1,10-seco-eudesmanolides (-)-eriolanin (1) and (-)-eriolangin (2) was achieved, which also established the hitherto unknown absolute configuration of these sesquiterpene lactones. Starting from 2-bromo-1-(2-furyl)ethanone, 24 steps were required to generate the common basic structure and two additional steps in each case for completion of the natural products. The effect of 1 and 2 on the cell cycle of human leukemia (HL-60) cells was investigated by flow cytometry. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).