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Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine
Authors:Moldvai Istvan  Gati Tamas  Szantay Csaba  Szantay Csaba
Affiliation:Department of Natural Organic Compounds, Chemical Research Center of the Hungarian Academy of Sciences, Institute of Bimolecular Chemistry, H-1525 Budapest, POB 17, Hungary. imoldvai@chemres.hu
Abstract:beta-Iodo-enamines with an eburnane skeleton (5a and 5c) were obtained with the aid of iodine from compounds 2a and 2c and were then transformed into hydroxyl lactams (6a and 6c) with CuSO4.5H2O in a mixture of DMF and water. Lactams (6a and 6c) were reduced selectively with BH3.SMe2 to result in the first synthesis of (-)-vincapusine (4a) as well as its natural 14-decarbomethoxy analogue (4c).
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