Studies related to maytansinoids

Abstract

(3R, 4R, 5R)-3-Benzoyloxy-4,5-dihydroxycylohexanone ethylene dithioacetal (10), a compound elaborated from D-(–)-quinic acid, was cleaved at the cis-diol position by the use of triphenylbismuth carbonate. The resulting dialdehyde (11) was converted, in several steps via the diol (12), into (2R)-1-benzoyloxy-2-carbamoyloxy-7,9-dioxadecan-4-one ethylene dithioacetal (19). Removal of the ethylene dithioacetal group using phenylseleninic anhydride afforded the acyclic (2R)-benzoyloxy-2-carbamoyloxy-7,9-dioxadecan-4-one (21). The enantiomer of the diol (12) was also prepared from D-(–)-quinic acid, as was the target ethylene dithioacetal (28).