Synthesis of (±)-chamobtusin A by a presumed biomimetic aza-cyclization

Organic Letters

Volumn 12, Issue 21, 2010, Pages 4709-4711

  Kuzuya, Kazuma ^a   Mori, Naoki ^a   Watanabe, Hidenori ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIAL; CHAMOBTUSIN A; DITERPENE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; BIOMIMETIC MATERIALS; CYCLIZATION; DITERPENES; MOLECULAR STRUCTURE;

EID: 78049492519     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101846z     Document Type: Article

References (18)

1. Zhang, Y.-M.; Tan, N.-H.; Lu, Y.; Chang, Y.; Jia, R.-R. Org. Lett. 2007, 9, 4579-4581
2. Conner, A. H.; Nagasampagi, B. A.; Rowe, J. W. Phytochemistry 1980, 19, 1121-1131
3. Alvarez-Manzaneda, E. J.; Chahboun, R.; Guardia, J. J.; Lachkar, M.; Dahdouh, A.; Lara, A.; Messouri, I. Tetrahedron Lett. 2006, 47, 2577-2580
4. For reviews, see
5. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
6. Xu, L.-W.; Xia, C.-G. Eur. J. Org. Chem. 2005, 633-639
7. Vicario, J. L.; Badía, D.; Carrillo, L.; Etxebarria, J.; Reyes, E.; Ruiz, N. Org. Prep. Proc. Int. 2005, 37, 513-538
8. Kobayashi, N.; Kuniyoshi, H.; Ishigami, K.; Watanabe, H. Biosci. Biotechnol. Biochem. 2008, 72, 2708-2715
9. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585
10. Other methods for preparing 3 have been reported. See
11. Razmilic, I.; Sierra, J.; Lopez, J.; Cortes, M. Chem. Lett. 1985, 1113-1114
12. Hueso-Rodrigues, J. A.; Rodrigues, B. Tetrahedron 1989, 45, 1567-1576
13. Abad, A.; Agulló, C.; Cuñat, A. C.; Pardo, D. Tetrahedron Lett. 2003, 44, 1899-1902
14. 1H NMR chemical shifts with those of similar compounds.
15. Benites, J.; Preite, M. D.; Cortés, M. Synth. Commun. 2001, 31, 1347-1354
16. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666
17. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156
18. Krafft, G. A.; Garcia, E. A.; Guram, A.; O'Shaughnessy, B.; Xu, X. Tetrahedron Lett. 1986, 27, 2691-2694