Enantioselective Synthesis and Absolute Configuration of (R)-(+)-Lunacridine and (S)-(+)-Lunacrine

Abstract

(R)-(+)-Lunacridine 1 has been synthesised in 97.3% e.e. using a chiron approach through L-valine and D-mannitol as the starting compounds in order to corroborate its absolute configuration.

References

1. J. R. Price, Aust. J. Chem., 1959, 12, 458; S. Goodwin and E. C. Horning, J. Am. Chem. Soc., 1959, 81, 1908; H. C. Beyerman and R. W. Rooda, Proc. K. Ned. Akad. Wet., Ser. B, 1959, 62, 187; S. Goodwin, A. F. Smith, A. A. Velasquez and E. C. Horning, J. Am. Chem. Soc., 1959, 81, 6209.
2. S. Goodwin, J. N. Shoolery and L. F. Johnson, J. Am. Chem. Soc., 1959, 81, 3065.
3. E. A. Clarke and M. F. Grundon, J. Chem. Soc., 1964, 438; R. Oels, R. Storrer and D. W. Young, J. Chem. Soc., Perkin Trans. 1, 1977, 2546.
4. R. M. Bowman, G. A. Gray and M. F. Grundon, J. Chem. Soc., Perkin Trans. 1, 1973, 1051.
5. S. A. Barr, D. R. Boyd, N. D. Sharma, T. A. Evans, J. F. Malone and V. D. Mehta, Tetrahedron, 1994, 50, 11219.
6. R. C. Anand and N. Selvapalam, Synth. Commun., 1994, 24, 1994.
7. A. Chattopadhyay and V. R. Mamdapur, J. Org. Chem., 1995, 60, 585.