Novel assembly of cyclic ethers by coupling alpha-chlorosulfides and alcohols.
A novel protocol for assembling polycyclic ethers was developed and successfully applied to the synthesis of the EFGH ring system of ciguatoxin CTX3C. A key transformation involves construction of an O,S-acetal through coupling of alpha-chlorosulfide and a secondary alcohol under mild conditions. The method is highly applicable to use with sensitive substrates and will enable the synthesis of various natural and artificial polycyclic ethers. [reaction: see text]
D000438:Alcohols / Q000737:chemistry*; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013440:Sulfides / Q000737:chemistry*
D000438:Alcohols; D004988:Ethers, Cyclic; D013440:Sulfides; D002922:Ciguatoxins