Acylnitrilium ion initiated heteroannulations in alkaloid synthesis. An efficient, stereocontrolled, total synthesis of the Orchidaceae alkaloid (±)-dendrobine

Article abstract of DOI:10.1021/ja00037a009

A concise total synthesis of (±)-dendrobine is described that proceeds in eight steps from 2-methylcyclopent-2-en-1-one. The key transformation in this approach is the silver ion mediated cyclocondensation of the isonitrile 6 with the acyl chloride 5. Thi