A scalemic synthesis of the scopadulcic acid skeleton. I: An efficient γ-alkylation at C-9 in abietane framework and subsequent aldol reaction

Article abstract of DOI:10.1016/0040-4039(96)01947-8

The first example of a carbon-carbon bond formation at C-9 in the abietane framework via a highly practical γ-alkylalion of the enone 6 is reported. Attempted intra-molecular aldol reaction of the derived enone aldehyde 13 gave exclusively the undesired product 14. However, the 12-methyl enone aldehyde 17 gave a trace of the desired aldol 19, bond formation at C-7 still being the major pathway.