16821-33-3Relevant articles and documents
CONTROLLING BENZYLIC FUNCTIONALITY AND STEREOCHEMISTRY: 2. SYNTHESIS OF THE PSEUDOPTEROSIN AGLYCONE
McCombie, Stuart W.,Cox, Brian,Ganguly, Ashit K.
, p. 2087 - 2090 (1991)
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).