A facile and efficient synthesis of 3, 3-dimethyl isopropylidene proline from (+)-3-carene

…, J Wong, J Kong, X Fu, V Girijavallabhan

Index: Nair, Latha G.; Saksena, Anil; Lovey, Raymond; Sannigrahi, Mousumi; Wong, Jesse; Kong, Jianshe; Fu, Xiaoyong; Girijavallabhan, Viyyoor Journal of Organic Chemistry, 2010 , vol. 75, # 4 p. 1285 - 1288

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Citation Number: 7

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.