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Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine.

The Journal of organic chemistry (2006-05-06)
Istvan Moldvai, Tamas Gati, Csaba Szantay, Csaba Szantay
RESUMEN

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).