An expeditious enantiospecific total synthesis of (+)-7-epi-goniofufurone

Synlett

Volumn , Issue 14, 2005, Pages 2260-2262

  Prasad, Kavirayani R ^a   Gholap, Shivajirao L ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

(+) goniofufurone; Stereoselective reduction; Styryl lactones

Indexed keywords

7 EPIGONIOFUFURONE; GONIOFUFURONE; LACTONE DERIVATIVE; STYRYLLACTONE; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 24744435960     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871965     Document Type: Article

References (28)

1. For a review on styryllactones from Goniothalamus species see: Blàzquez, M. A.; Bermejo, A.; Zafra-Polo, M. C.; Cortes, D. Phytochem. Anal. 1999, 10, 161.
2. (a) Fang, X. P.; Anderson, J. E.; Chang, C. J.; Fanwick, P. E.; McLaughlin, J. L. J. Chem. Soc., Perkin. Trans. 1 1990, 1655.
3. (b) Fang, X. P.; Anderson, J. E.; Chang, C. J.; McLaughlin, J. L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034.
4. (c) Fang, X. P.; Anderson, J. E.; Chang, C. J.; McLaughlin, J. L. Tetrahedron 1991, 47, 9751.
5. For a review on the cytotoxic activity and other bioactivity of styryl lactones, see: Mereyala, H. B.; Joe, M. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 293.
6. (a) Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007.
7. (b) Murphy, P. J.; Dennison, S. T. Tetrahedron 1993, 49, 6695.
8. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359.
9. (d) Xu, D.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 4685.
10. (e) Yang, Z. C.; Zhou, W. S. Tetrahedron 1995, 51, 1429.
11. (f) Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101.
12. (g) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472.
13. (h) Fernandez de la Pradilla, R.; Montero, C.; Priego, J.; Martinez-Cruz, L. A. J. Org. Chem. 1998, 63, 9612.
14. (i) Bruns, R.; Wernicke, A.; Koll, P. Tetrahedron 1999, 55, 9793.
15. (j) Surivet, J.-P.; Vatele, J.-M. Tetrahedron 1999, 55, 13011.
16. Shing, T. K. M.; Tsui, H. C.; Zhou, Z. H. J. Org. Chem. 1995, 60, 3121.
17. (a) Prakash, K. R. C.; Rao, S. P. Tetrahedron 1993, 49, 1505.
18. (b) Prakash, K. R. C.; Rao, S. P. Synlett 1993, 123.
19. Mukai, C.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547.
20. Tsubuki, M.; Kanai, K.; Nagase, H.; Honda, T. Tetrahedron 1999, 55, 2493.
21. (a) Mereyala, H. B.; Gadikota, R. R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39, 166.
22. (b) Mereyala, H. B.; Gadikota, R. R.; Joe, M.; Arora, S. K.; Dastidar, S. G.; Agarwal, S. Bioorg. Med. Chem. 1999, 7, 2095.
23. Su, Y.-L.; Yang, C.-S.; Teng, S.-J.; Zhao, G.; Ding, Y. Tetrahedron 2001, 57, 2147.
24. (a) Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
25. (b) Seebach, D.; Hidber, A. Org. Synth., Coll. Vol. 7; Wiley: New York, 1990, 447.
26. The minor isomer was removed by simple crystallization from hexane-EtOAc.
27. We anticipated that the addition of vinyl magnesiumbromide to 9 followed by a stereoselective reduction of the ketone and RCM would yield the intermediate 14. However, addition of vinyl magnesium bromide to 9 proceeded with low yield. Full details of this strategy will be discussed in a future article.
28. 5Si: C, 65.31; H, 7.97. Found: C, 65.26; H, 7.80.