Synthesis of the Putative Structure of Eupomatilone-6

Organic Letters

Volumn 6, Issue 3, 2004, Pages 317-319

  Gurjar, Mukund K ^a   Cherian, Joseph ^a   Ramana, C V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EUPOMATILONE 6; KETONE DERIVATIVE; LIGNAN DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIHYDROXYLATION; HORNER WADSWORTH EMMONS REACTION; MOLECULAR DYNAMICS; SPECTROSCOPY; SUZUKI REACTION; SYNTHESIS;

ANGIOSPERMS; BENZOFURANS; LIGNIN; MOLECULAR STRUCTURE;

EID: 1342306680     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035908j     Document Type: Article

References (15)

1. Taylor, W. C.; Carroll, A. R. Aust. J. Chem. 1991, 44, 1615-1626.
2. (a) Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
3. (b) Macrae, W. D.; Towers, G. H. N. Phytochemistry 1984, 23, 1207-1220.
4. Hong, S.; McIntosh, M. C. Org. Lett. 2002, 4, 19-21.
5. Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1-6.
6. Li, J. J.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Collins, J. T.; Garland, D. J.; Gregory, S. A.; Huang, H.-C.; Isakson, P. C.; Koboldt, C. M.; Logusch, E. W.; Norton, M. B.; Perkins, W. E.; Reinhardt, E. J.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y.; Reitzt, D. B. J. Med. Chem. 1995, 38, 4570-4578.
7. Ziegler, F. E.; Chliwner, I.; Fowler, K. W.; Kanfer, S. J.; Kuo, S. J.; Sinha, N. D. J. Am. Chem. Soc. 1980, 102, 790-798.
8. Ni(0) catalyst-mediated Negishi coupling had been used for the preparation of 7: Larson, E. R.; Raphael, R. A. J. Chem. Soc., Perkin Trans. 1 1982, 521-525.
9. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
10. For a review of butenolide synthesis, see: Rao, Y. S. Chem. Rev. 1976, 76, 625-694.
11. (a) Katsumura, S.; Kimura, A.; Isoe, S. Tetrahedron 1989, 45, 1337-1346.
12. (b) Nangia, A.; Prasuna, G. Tetrahedron 1996, 52, 3435-3450.
13. (c) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfield, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
14. We have noticed that the epimerization happens mainly during the conversion of 13 to 15. For analytical purposes, we have synthesized (±)-16 from 8E by following the same sequence of reactions but with an achiral dihydroxylation step and showed it to be a 1:1 racemic mixture by performing HPLC analysis on a Chiralcel-OD column using 5% 2-propanol in hexane.
15. Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190.