Journal of Organic Chemistry p. 4659 - 4661 (1985)
Update date:2022-07-29
Topics:
Tsang, Raymond
Fraser-Reid, Bert
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.
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