Antileukemic pyrone 1 was synthesized by way of a five-step procedure from 4-Hydroxy-5-methoxycarbonyl-6-methyl-2-pyrone (8). This is the first synthesis of 4-methoxy-6-methyl-5-(3-oxobutyl)-2H-pyran-2-one (1).
MarrisonLR, DickinsonJM, AhmedR, FairlambIJ. (2002). An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone. Tetrahedron Letters, 43, 8853–8857.
9.
HsungR, KurdyumovA, MuñozR. (2006) Total syntheses of daldiniapyrone, annularin B, and (±)-annularin F. Synthesis, 11, 1787–1790.
10.
ShimizuT, HiranumaS, WatanabeT. (1993) Reduction of α-Pyrone derivatives with borane-methyl sulfide complex. Heterocycles, 36, 2445–2450.
