Beilstein J. Org. Chem.2022,18, 1741–1748, doi:10.3762/bjoc.18.183
’-methoxy-γ-pyrone in one step. To construct the quaternary carbon of the 2,5-cyclohexadienone of the target, a strategy based on the Robinson-type annulation of an aldehyde derived from α-crotyl-α’-methoxy-γ-pyrone was applied. The grafting of the simplified target’s side chain was demonstrated through an
oxidative anionic oxy-Cope rearrangement of the tertiary alcohol arising from the 1,2-addition of a 1,3-dimethylallyl reagent to 2,5-cyclohexadienone connected to the α’-methoxy-γ-pyrone motif.
Keywords: α’-methoxy-γ-pyrone; 2,5-cyclohexadienone; oxy-Cope; quaternary carbon; Robinson-type annulation
; Introduction
The α’-methoxy-γ-pyrone motif is present in natural products and bioactive molecules [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Amidst these targets, a number contains a quaternary carbon vicinal to the scaffold, such as crispatene and photodeoxytridachione (Scheme 1a) [15]. These molecules
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Graphical Abstract
Scheme 1:
Routes to crispatene, photodeoxytridachione, aureothin, and tridachiapyrone B.