Tetrahedron Letters p. 1317 - 1320 (1997)
Update date:2022-09-26
Topics:
Subasinghe, Nalin L.
Khalil, Ehab M.
Johnson, Rodney L.
Bicyclic thiazolidine lactam 1 was used as a model system for developing synthetic methodology into β-turn mimics that would contain side chain functionality. Treatment of a mixture of 1 and a non-enolizable aldehyde at -100°C with LDA resulted in a good yield of the aldol adduct when aromatic aldehydes were used. Radical dehydroxylation of the pentafluorophenylcarbonate derivative of the aldol adduct with (n-Bu)3SnH and AIBN gave a single isomer of the C-2 alkylated bicyclic 5,5-thiazolidine lactam. This methodology was applied to the synthesis of the 2-substituted spiro bicyclic thiazolidine lactam type II' β-turn mimic 14.
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Doi:10.1021/jm960858s
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(1968)