Stereocenter

Organic chemistry

Ring (chemistry)

Stereochemistry

Enantioselective synthesis

Catalysis

Alkylation

Stereoselectivity

Chemistry

Claisen rearrangement

Nitrile

Intramolecular force

Synlett

Synthetic studies on an ABC-ring model of tubiferal A, a triterpenoid isolated from the fruit bodies of the Tubifera dimorphotheca myxomycete, are described. The stereogenic centers at the angular positions were constructed through the stereoselective addition of a C-ring allylborane followed by an Eschenmoser–Claisen rearrangement reaction prior to the formation of the AB-ring system by a double intramolecular alkylation reaction of a dichloro nitrile intermediate.

Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-Ring Compound