805239-91-2Relevant academic research and scientific papers
Diastereoselective phenol para-alkylation: Access to a cross-conjugated cyclohexadienone en route to resiniferatoxin
Ritter, Tobias,Zarotti, Pablo,Carreira, Erick M.
, p. 4371 - 4374 (2007/10/03)
(Chemical Equation Presented) We document a route for the synthesis of a densely functionalized spiro-fused 2,5-cyclohexadienone as an intermediate for the synthesis of resineferatoxin. The strategy is based on an unprecedented diastereoselective, intramolecular phenol para-alkylation to a cross-conjugated cyclohexadienone. In the course of these synthetic studies we developed rapid access to a chiral nitrile possessing a quaternary stereocenter and disclose an unusual acetal rearrangement from a dioxane, which favors the corresponding dioxepane.
