Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2

Article abstract of DOI:10.1016/S0040-4039(98)02400-9

The MOM protected keto alcohol 7 was successfully converted to the silyl enol ether 4 by reaction with BSA. Reaction of this intermediate with dioxirane led to formation of allylic alcohol 10. Lactone 15 was obtained by reaction of tosylate 14 with the cuprate reagent derived from ethyl bromoacetate. Through a short sequence of reactions this 5-membered lactone was isomerized to the target lactone product 18.