A Route to Optically Active Trichothecane Skeleton by Bisannulation of a Pyranose Derivative

Article abstract of DOI:10.1021/jo00223a053

A process has been developed for bisannulation of a pyranose ring to produce the trichothecene skeleton in which (a) the cyclohexeno (A) ring is connected at C1/C2 of the sugar, (b) an Eschenmoser-Claisen rearrangement is applied at C3 to generate an equatorially oriented acetamido unit, and (c) the activated methylene group is used to displace a sulfonate at C6 of the original sugar in a process that forms the C ring.