Journal of Organic Chemistry 2010-02-19

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

Latha G Nair, Anil Saksena, Raymond Lovey, Mousumi Sannigrahi, Jesse Wong, Jianshe Kong, Xiaoyong Fu, Viyyoor Girijavallabhan

Index: J. Org. Chem. 75(4) , 1285-8, (2010)

Full Text: HTML

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.

Related Compounds

  • (+)-D-3-Carene
  • carene

Related Articles:

Mechanisms for the formation of organic acids in the gas-phase ozonolysis of 3-carene.

2009-06-07

[Phys. Chem. Chem. Phys. 11(21) , 4184-97, (2009)]

Antioxidant and antiacetylcholinesterase activities of some commercial essential oils and their major compounds.

2011-01-01

[Molecules 16(9) , 7672-90, (2011)]

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1S)-(+)-3-carene derived tricyclic iminolactone.

2011-03-18

[J. Org. Chem. 76(6) , 1621-33, (2011)]

Sensitive monitoring of monoterpene metabolites in human urine using two-step derivatisation and positive chemical ionisation-tandem mass spectrometry.

2013-09-02

[Anal. Chim. Acta 793 , 26-36, (2013)]

Low concentration of 3-carene stimulates the differentiation of mouse osteoblastic MC3T3-E1 subclone 4 cells.

2008-01-01

[Phytother Res. 22(1) , 18-22, (2008)]

More Articles...