An asymmetric synthesis of (+)-erysotramidine

Synthesis

Volumn , Issue 19, 2005, Pages 3287-3292

  Blake, Alexander J ^a   Gill, Christopher ^a   Greenhalgh, Daniel A ^a   Simpkins, Nigel S ^a   Zhang, Fengzhi ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Alkaloid; Asymmetric synthesis; Chiral base; Erythrinan; Radical reaction

Indexed keywords

CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

ALKALOID; ASYMMETRIC SYNTHESIS; CHIRAL BASE; ERYTHRINAN; RADICAL REACTION;

NITROGEN COMPOUNDS;

ALKALOID DERIVATIVE; ERYSOTRAMIDINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; RADICAL REACTION; SYNTHESIS;

EID: 29044435289     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918478     Document Type: Article

References (25)

1. For reviews, see: (a) Bentley, K. W. The Isoquinoline Alkaloids; Harwood Academic Publishers: Amsterdam, 1998.
2. (b) Bentley, K. W. Nat. Prod. Rep. 2005, 22, 249.
3. (c) Tsuda, Y.; Sano, T. In The Alkaloids, Vol. 48; Cordell, G. A., Ed.; Academic Press: New York, 1996, 249-337.
4. For recent contributions and leading references, see: (a) Padwa, A.; Lee, H. L; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2004, 69, 8209.
5. (b) Yasui, Y.; Koga, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, 615.
6. (c) Reimann, E.; Ettmayr, C. Monatsh. Chem. 2004, 135, 959.
7. (d) Osante, I; Sotomayor, N.; Lete, E. Lett. Org. Chem. 2004, 1, 323.
8. (e) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047.
9. (a) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
10. (b) Allin, S. M.; Streetley, G. B.; Slater, M.; James, S. L.; Martin, W. P. Tetrahedron Lett. 2004, 45, 5493.
11. (c) Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, 619; and references cited therein.
12. Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803.
13. Ito, K.; Furukawa, H.; Haruna, M. Yakugaku Zasshi 1973, 93, 1617;
14. Chem. Abstr. 1974, 80, 48212.
15. Gonzalez-Temprano, I.; Sotomayor, N.; Lete, E. Synlett 2002, 593.
16. Adams, D. J.; Blake, A. J.; Cooke, P. A.; Gill, C. D.; Simpkins, N. S. Tetrahedron 2002, 58, 4603.
17. Manteca, I.; Etxarri, B.; Ardeo, A.; Arrasate, S.; Osante, I.; Sotomayor, N.; Lete, E. Tetrahedron 1998, 54, 12361.
18. Yu, W.; Mei, Y.; Rang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217.
19. Muller, E.; Gasparutto, D.; Jaquinod, M.; Romieu, A.; Cadet, J. Tetrahedron 2000, 56, 8689.
20. This mixture of epimeric alcohols has been reported previously in racemic form, see: Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Bottcher, K. Chem. Ber. 1970, 103, 615.
21. (a) Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
22. (b) Togo, H. Advanced Free Radical Reactions for Organic Synthesis; Elsevier: Amsterdam, 2004.
23. Burgess, E. M.; Penton, H. R.; Taylor, H. R. J. J. Org. Chem. 1973, 38, 26.
24. 2 oxidation.
25. Moffat, D.; Nichols, C. J.; Riley, D. A.; Simpkins, N. S. Org. Biomol. Chem. 2005, 3, 2953.