Stereospecific synthesis of 2-substituted bicyclic thiazolidine lactams

✍ Scribed by Nalin L. Subasinghe; Ehab M. Khalil; Rodney L. Johnson

• Book ID: 104256440
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 259 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00067-1

✦ Synopsis

Bicyclic thiazolidine lactam 1 was used as a model system for developing synthetic methodology into ~-tm'n 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 ~d,_,ct when aromatic aldehydes we~'e used. Radical dehydroxylation of the pentafluorophenyicarbonate de0rivative of the aldol a_dd~ct with (n-Bu)3SnH and AIBN gave a single isomer of the C-2 alkylated bicyelic 5,5-thiaTolidine lactmn. This methodology was applied to the synthesis of the 2-substituted spiro bicyclic thiazofidine laclam type II' IS-turn mimic 14.