The efficient entry into the tricyclic core of halichlorine

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 929-932

  Shindo, Mitsuru ^a   Fukuda, Yu Ichi ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Alkaloids; Cycloadditions; Marine metabolites; Mitsunobu reactions

Indexed keywords

ALKALOID DERIVATIVE; HALICHLORINE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034607019     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02192-9     Document Type: Article

References (16)

1. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3870.
2. Chou, T.; Kuramoto, M.; Otani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871-3874.
3. For the absolute structure of halichlorine; Arimoto, H.; Hayakawa, I.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1998, 39, 861-862.
4. Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583-3586.
5. (a) Lee, S.; Zhao, Z. Organic Lett. 1999, 1, 681-683.
6. (b) Very recently, they also reported a similar approach to the azaspiro core: Lee, S.; Zhao, Z. Tetrahedron Lett. 1999, 40, 7921-7924.
7. Trauner, D.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513-6516.
8. Keen, S. P.; Weinreb, S. M. J. Org. Chem. 1998, 63, 6739-6741.
9. (a) Grigg, R.; Markandu, J.; Surendrakumar, S.; Thornton Pett, M.; Warnock, W. J. Tetrahderon 1992, 48, 10399-10422.
10. (b) Armstrong, P.; Grigg, R.; Surendrakumar, S.; Warnock, W. J. Chem. Soc., Chem. Commun. 1987, 1327-1328.
11. (c) Armstrong, P.; Grigg, R.; Warnock, W. J. Chem. Soc., Chem. Commun. 1987, 1325-1327.
12. -1. The final refinement converged to R=0.058 and Rw=0.076 for 184 parameters.
13. The stereochemistries were determined by NOE experiments.
14. Tsunoda, T.; Nagino, C.; Oguri, M.; Ito, S. Tetrahedron Lett. 1996, 37, 2459-2462.
15. When the reaction was conducted using diethyl malonate, the coupled product 14 was obtained in only 13% yield because of competitive O alkylation.
16. Couladouros, E. A.; Moutsos, V. I. Tetrahedron Lett. 1999, 40, 7027-7030.