CONTROLLING BENZYLIC FUNCTIONALITY AND STEREOCHEMISTRY: 2. SYNTHESIS OF THE PSEUDOPTEROSIN AGLYCONE

Article abstract of DOI:10.1016/S0040-4039(00)71243-3

Homologation, cyclisation, and reduction converted the tetralin (2) to the hexahydrophenalenol (8), which was methylated to afford (19) via alkoxide-directed metallation.The degree of stereoselectivity resulting from reactions of (19) and congeners with allylsilane - Lewis acid combinations was markedly dependent upon substitution patterns, whereas Et2AlCN-SnCl4 produced pseudoaxial nitriles.The trimethyl nitrile (24) was elaborated to the pseudopterosin aglycone (4).