Efficient total syntheses of phytoalexin and (±)-paniculidine B and C based on the novel methodology for the preparation of 1-methoxyindoles

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4429-4432

  Selvakumar, N ^a   Rajulu, G Govinda ^a,b  

^a DR REDDY'S LABORATORIES LTD   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

NATURAL PRODUCTS; PHYTOALEXINS;

AROMATIC HYDROCARBONS;

1 METHOXYINDOLE; ALDEHYDE; INDOLE DERIVATIVE; NATURAL PRODUCT; PANICULIDINE B; PANICULIDINE C; PHYTOALEXIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; QUANTUM YIELD; REACTION ANALYSIS;

INDOLES; MOLECULAR STRUCTURE; PLANT EXTRACTS; TERPENES;

EID: 3042784995     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040134l     Document Type: Article

References (16)

1. (a) Somei, M. Heterocycles 1999, 50, 1157.
2. (b) Acheson, R. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, CA, 1990; Vol. 51, pp 105-175.
3. Soledade, M.; Pedras, C.; Sorenson, J. L. Phytochemistry 1998, 49, 1959.
4. Kinoshita, T.; Tatara, S.; Ho, F.-C.; Sankawa, U. Phytochemistry 1989, 28, 147 and references therein.
5. (a) Selvakumar, N.; Reddy, B. Y.; Azhagan, A. M.; Khera, M. K.; Babu, J. M.; Iqbal, J. Tetrahedron Lett. 2003, 44, 7065.
6. (b) Selvakumar, N.; Khera, M. K.; Reddy, B. Y.; Srinivas, D.; Azhagan, A. M.; Iqbal, J. Tetrahedron Lett. 2003, 44, 7071.
7. 2Me) also resulted in the corresponding decarboxylated product. These results ascertained the requirement of an activated methylene group for the key cyclization step. [Diagram presented]
8. For a synthesis of this phytoalexin, see: Somei, M.; Tanimato, A.; Orita, H.; Yamada, F.; Ohata, T. Heterocycles 2001, 54, 425. For a synthesis of paniculidine B, see: Somei, M.; Ohnishi, H. Chem. Pharm. Bull. 1985, 33, 5147.
9. For a synthesis of this phytoalexin, see: Somei, M.; Tanimato, A.; Orita, H.; Yamada, F.; Ohata, T. Heterocycles 2001, 54, 425. For a synthesis of paniculidine B, see: Somei, M.; Ohnishi, H. Chem. Pharm. Bull. 1985, 33, 5147.
10. For decarboxylation of indole-2-carboxylic acids, see: Jones, G. B.; Chapman, B. J. J. Org. Chem. 1993, 58, 5558 and references therein.
11. Pawlak, J. L.; Berchtold, G. A. J. Org. Chem. 1988, 53, 4063.
12. Gribble, G. W.; Leese, R. M. Synthesis 1977, 172.
13. Patiki, J.; Harvey, R. G. J. Org. Chem. 1987, 52, 2226.
14. Sakai, T.; Miyata, K.; Utaka, M.; Jakeda, A. Tetrahedron Lett. 1987, 28, 3817.
15. Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A. Bull. Chem. Soc. Jpn. 1988, 61, 285.
16. Morimoto, H.; Oshio, H. Justus Liebigs Ann. Chem. 1965, 682, 212.