Tetrahedron Letters p. 2087 - 2090 (1991)
Update date:2022-08-05
Topics:
McCombie, Stuart W.
Cox, Brian
Ganguly, Ashit K.
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).
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