Total synthesis of coriandrin and 7-demethylcoriandrin via a new synthesis of isocoumarins

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3677-3680

  Mal, Dipakranjan ^a   Bandyopadhyay, Mousumi ^a   Ghorai, Sujit K ^a   Datta, Kalyani ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Coriandrin; Epoxide; Isocoumarins; Thermal rearrangement

Indexed keywords

7 DEMETHYLCORIANDRIN; CORIANDRIN; ISOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034611956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00441-X     Document Type: Article

References (20)

1. Ceska, O.; Chaudhary, S. K.; Warrington, P.; Ashwood-Smith, M. J.; Bushnell, G. W.; Poulton, G. A. Phytochem. Photobiol. 1988, 27, 2083.
2. Hudson, J. B.; Graham, E. A.; Harris, L.; Ashwood-Smith, M. J. Photochem. Photobiol. 1993, 57, 491.
3. Kraus, G.; Ridgeway, J. J. Org. Chem. 1994, 59, 4735.
4. Mal, D.; Bandhopadhay, M.; Datta, K.; Murty, K. V. S. N. Tetrahedron 1998, 54, 7525.
5. (a) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579.
6. (b) Mal, D.; Hazra, N. K.; Murty, K. V. S. N.; Majumdar, G. Synlett 1995, 1239.
7. (c) Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 37, 8953.
8. (d) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647.
9. (e) Bandhopadhay, M.; Datta, K.; Mal, D. J. Ind. Chem. Soc. 1999, 76, 551.
10. Houwen-Claassen, A. A. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1989, 45, 7134.
11. (a) Hauser, F. M.; Baghdanov, V. M. J. Org. Chem. 1988, 53, 4676.
12. (b) Wang, L.; Shen, W. Tetrahedron Lett. 1998, 39, 7625.
13. (c) Mali, R. S.; Babu, K. N. J. Org. Chem. 1998, 63, 2488, and references cited therein.
14. (a) Lewis, C. N.; Staunton, J.; Sunter, D. C. J. Chem. Soc., Perkin Trans. 1 1988, 747.
15. (b) Kelly, T. R.; Jagoe, C. R.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522.
16. (c) Yamaguchi, M.; Okuma, T.; Horiguchi, A.; Ikeura, C.; Minami, T. J. Org. Chem. 1992, 57, 1647.
17. (d) Nomoto, S.; Mori, K. Liebigs Ann. 1997, 721.
18. (e) Thrash, T. P.; Welton, T. D.; Behar, V. Tetrahedron Lett. 2000, 41, 29.
19. Mal, D.; Ghorai, S. K.; Hazra, N. K. Terahedron Lett. 1998, 39, 689.
20. +), 201 (100%), 187, 159, 144, 129, 116.