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Total synthesis of (+/-)-jamtine using a thionium/N-acyliminium ion cascade
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA. chemap@emory.edu
Organic Letters
|March 1, 2002
Abstract:
[reaction: see text] 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.