Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates: a model study for the Tacaman alkaloid D/E ring fusion

✍ Scribed by Roger Hunter; Philip Richards

• Book ID: 104210273
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 110 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00485-8

✦ Synopsis

Stereoselective cyclisation of malic acid-derived α-sulfanyllactam (1) via radical and carbanionic intermediates affords stereo-defined tetrahydropyrido[2,1-a]isoindolones as model compounds for the D/E cis-ring fusion of the Tacaman indole alkaloid skeleton. A transition-state model to explain the stereoselectivity is presented.