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Controlling benzylic functionality and stereochemistry: 2. Synthesis of the pseudopterosin aglycone
journal contribution
posted on 2023-06-08, 19:32 authored by Stuart W McCombie, Brian Cox, Ashit K GangulyHomologation, 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).
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Publication status
- Published
Journal
Tetrahedron LettersISSN
0040-4039Publisher
ElsevierExternal DOI
Issue
19Volume
32Page range
2087-2090Department affiliated with
- Chemistry Publications
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- No
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- Yes
Legacy Posted Date
2015-01-14Usage metrics
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