Controlling benzylic functionality and stereochemistry: 2. Synthesis of the pseudopterosin aglycone

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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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
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://sro.sussex.ac.uk/id/eprint/52125
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