A stereoselective formal total synthesis of (+)-hyperaspine via a tandem aza-Michael reaction

Tetrahedron Letters

Volumn 48, Issue 39, 2007, Pages 6924-6927

  Radha Krishna, Palakodety ^a   Sreeshailam, A ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(+) Hyperaspine; 3 Oxaquinolizidine skeleton; Benzylamine; Chiral allylation; Dienone; One pot double aza Michael addition

Indexed keywords

ALKALOID DERIVATIVE; HYPERASPINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34548329838     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.184     Document Type: Article

References (16)

1. Lebrun B., Braekman J.-C., Daloze D., Kalushkov P., and Pasteels J.M. Tetrahedron Lett. 42 (2001) 4621-4623
2. Zhu W., and Ma D. Org. Lett. 5 (2003) 5063-5066
3. Dooms C., Laurent P., Daloze D., Pasteels J., Nedved O., and Braekman J.-C. Eur. J. Org. Chem. (2005) 1378-1383
4. Commins D., and Sahn J.J. Org. Lett. 7 (2005) 5227-5228
5. For an 8-epimer synthesis, please see:. Ma D., and Zhu W. Tetrahedron Lett. 44 (2003) 8609-8612
6. Radha Krishna P., and Krishnarao L. Synlett (2007) 1742-1745
7. Radha Krishna, P.; Dayaker, G. Unpublished results.
8. Reetz M.T., and Jung A. J. Am. Chem. Soc. 105 (1983) 4833-4835
9. Perlmutter P. In: Baldwin J.E., and Magnus P.D. (Eds). Conjugate Addition Reactions in Organic Synthesis. Tetrahedron Organic Chemistry Series Vol. 9 (1992), Pergamon, Oxford
10. Schäfer M., Drauz K., and Schwarm M. Methoden Org. Chem. 4th ed. Vol. E21/5 (1995), Houben-Weyl pp 5588-5642
11. Enders D., Wahl H., and Bettray W. Angew. Chem., Int. Ed. Engl. 34 (1995) 453-457 and references cited therein
12. 2d as follows:{A figure is presented}
13. It is logical to think that if the initial aza-Michael reaction were to occur on the β-carbon of the dienone nearer to the alkyl substituent the product ratio would have altered to 1:1 in favor of 2 and its C-8 epimer considering that the exclusive anti-selectivity of the second Michael reaction is still retained. Since the C-8 epimeric product was never observed, this argument was discounted.
14. Yun H., Gagnon A., and Danishefsky S.J. Tetrahedron Lett. 47 (2006) 5311-5315
15. Zou W., Sandbhor M., and Bhasin M. J. Org. Chem. 72 (2007) 1226-1234
16. 3: C, 75.43; H, 9.50. Found: C, 75.27; H, 9.68.