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McCombie, Stuart W, Cox, Brian and Ganguly, Ashit K (1991) Controlling benzylic functionality and stereochemistry: 2. Synthesis of the pseudopterosin aglycone. Tetrahedron Letters, 32 (19). pp. 2087-2090. ISSN 0040-4039
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Official URL: http://dx.doi.org/10.1016/S0040-4039(00)71243-3
Abstract
Homologation, cyclisation, and reduction converted the tetralin (2) to the hexahydrophenalenol (8), which was methylated to afford (19), via alkoxide-directed metalation. 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).
Item Type: | Article |
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Schools and Departments: | School of Life Sciences > Chemistry |
Subjects: | Q Science > QD Chemistry |
Depositing User: | Tom Gittoes |
Date Deposited: | 14 Jan 2015 10:22 |
Last Modified: | 14 Jan 2015 10:22 |
URI: | http://srodev.sussex.ac.uk/id/eprint/52125 |