Total Synthesis of (±)-Jamtine Using a Thionium/N-Acyliminium Ion Cascade

The first total synthesis of (±)-jamtine (4), a tetrahydroisoquinoline alkaloid reputed for its therapeutic properties, is described. The key step involves a tandem thionium/N-acyliminium ion cyclization from enamido sulfoxide 13. The cascade process takes place with high diastereoselectivity and in...

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Bibliographic Details
Published in:Organic letters 2002-03, Vol.4 (5), p.715-717
Main Authors: Padwa, Albert, Danca, M. Diana
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Anti-Infective Agents - chemical synthesis
Caproates - chemistry
Isoquinolines - chemical synthesis
Lactones - chemistry
Plants, Medicinal
Quaternary Ammonium Compounds - chemistry
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Summary:The first total synthesis of (±)-jamtine (4), a tetrahydroisoquinoline alkaloid reputed for its therapeutic properties, is described. The key step involves a tandem thionium/N-acyliminium ion cyclization from enamido sulfoxide 13. The cascade process takes place with high diastereoselectivity and in excellent yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol017193v