Enantiospecific total synthesis of (+)-lentiginosine

Arkivoc

Volumn 2010, Issue 6, 2010, Pages 39-46

  Prasad, Kavirayani R ^a   Pawar, Amit B ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Aza sugar; Lentiginosine; Stereoselective synthesis; Tartaric acid

Indexed keywords

EID: 77953405503     PISSN: 15517012     EISSN: 15517004     Source Type: None    
DOI: 10.3998/ark.5550190.0011.605     Document Type: Article

References (21)

1. Pastuszak, I.; Molynuex, R. J.; James, L.-F.; Elbein, A. D. Biochemistry 1990, 29, 1886.
2. For a review on aminosugars see: (a) Stutz, A. E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Wiley-VCH, 1999.
3. (b) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
4. (c) Asano, N. Glycobiology 2003, 13, 93R. For recent synthesis of (+)-lentiginosine see
5. (d) Alam, M. A.; Vankar, Y. D. Tetrahedron Lett, 2008, 49, 5534.
6. (e) Chen, M. J.; Tsai, Y. M. Tetrahedron Lett. 2007, 48, 6271.
7. (f) Cardona, F.; Moreno, G.; Guarna, F.; Vogel, P.; Schuetz, C.; Merino, P.; Goti, A. J. Org. Chem. 2005, 70, 6552.
8. (g) Raghavan, S.; Sreekanth, T. Tetrahedron: Asymmetry 2004, 15, 565.
9. (h) Feng, Z. H.; Zhou, W. S. Tetrahedron Lett. 2003, 44, 497.
10. (i) Rabiczko, J.; Urban, L. Z.; Chmielewski, M. Tetrahedron 2002, 58, 1433.
11. (j) Ha, D. C.; Yun, C. S.; Lee, Y. J. Org. Chem. 2000, 65, 621.
12. For a general approach to the synthesis of ã-keto amides from tartaric acid see: (a) Prasad, K. R.; Chandrakumar, A. Tetrahedron 2007, 63, 1798. For recent application of ã-keto amides derived from tartaric acid in natural product synthesis see
13. (b) Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2008, 73, 2.
14. (c) Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2008, 73, 2916.
15. (d) Prasad, K. R.; Swain, B. Tetrahedron: Asymmetry 2008, 19, 1134.
16. (e) Prasad, K. R.; Gandi, V. Tetrahedron: Asymmetry 2008, 19, 2616.
17. (f) Prasad, K. R.; Chandrakumar, A. J. Org. Chem. 2007, 72, 6312.
18. (g) Prasad, K. R.; Dhaware, M. Synthesis, 2007, 3697.
19. (h) Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2006, 71, 3643.
20. Formation of a minor amount (8%) of diketone resulting from the addition of Grignard reagent to both amide groups is observed.
21. The minor diastereomeric lactam is separable at this stage by column chromatography. No efforts were made to isolate and characterize the very small amounts of minor diastereomer.