A Facile and Efficient Synthesis of 3,3-Dimethyl Isopropylidene Proline From (+)-3-Carene
The Journal of Organic Chemistry2010Vol. 75(4), pp. 1285–1288
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Latha G. Nair, Anil K. Saksena, Raymond G. Lovey, Mousumi Sannigrahi, J.K.Y. Wong, Jianshe Kong, Xiaoyong Fu, Viyyoor Girijavallabhan
Abstract
A highly efficient and practical route to 3,4-isopropylidene proline I, starting from (+)-3-carene, was developed. The three continuous stereocenters were constructed using the inherent chirality of the starting natural product 2. The overall yield for the 12-step synthesis is 34%. The optimized sequence leading to 1 has been successfully applied on a multigram scale, thereby establishing the practicality of this route.
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