An enantiospecific formal total synthesis of the 5-8-5 tricyclic diterpene ent-fusicoauritone

Synlett

Volumn , Issue 1, 2012, Pages 123-127

  Srikrishna, A ^a   Nagaraju, Gopalasetty ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

cyclooctanoids; enantiospecific synthesis; fusicoccanes; limonene; ring closing metathesis

Indexed keywords

5 8 5 TRICYCLIC DITERPENE FUSICOAURITONE; 5 ISOPROPYK 2 METHYLCYCLOPENT 1 ENEMETHANOL; DITERPENE; FUSICOCCIN; METHANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; RING CLOSING METATHESIS;

EID: 84655176401     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290095     Document Type: Article

References (31)

1. Barrow K D., Barton D H. R., Chain E, Conlay C, Smale T C., Thomas R, Waight E S., J. Chem. Soc. C. 1971 1259
2. Barrow K D., Barton D H. R., Chain E, Ohnsorge U F. W., Thomas R, J. Chem. Soc. C 1971 1265
3. Tassa T, Togashi M, Agric. Biol. Chem. (Japan) 1973 37 1505
4. Huneck S, Baxter G, Cameron A F., Connolly J D., Rycroft D S., Tetrahedron Lett. 1983 24 3787
5. Asakawa Y, Lin X, Tori M, Kondo K, Phytochemistry 1990 29 2597
6. Zapp J, Burkhardt G, Becker H, Phytochemistry 1994 37 787
7. Liu H.-J, Wu C.-L, Becker H, Zapp J, Phytochemistry 2000 53 845
8. Komala I, Ito T, Nagashima F, Yagi Y, Kawahata M, Yamaguchi K, Asakawa Y, Phytochemistry 2010 71 1387
9. Gilabert M, Ramos A N., Schiavone M M., Arena M E., Bardon A, J. Nat. Prod. 2011 74 574
10. For detailed biological profiles of fusicoccins, see references cited in:, Richter A, Hedberg C, Waldmann H, J. Org. Chem. 2011 76 6694
11. Mehta G, Singh V, Chem. Rev. 1999 99 881
12. Petasis N A., Patane M A., Tetrahedron 1992 48 5757
13. Dake G R., Fenster E E., Patrick B O., J. Org. Chem. 2008 73 6711; and references cited therein
14. Williams D R., Robinson L A., Nevill C R., Reddy J P., Angew. Chem. Int. Ed. 2007 46 915
15. Srikrishna A, Babu N C., Tetrahedron Lett. 2001 42 4913
16. Srikrishna A, Babu N C., Dethe D H., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003 42 1688
17. Srikrishna A, Dethe D H., Org. Lett. 2003 5 2295
18. Srikrishna A, Babu N C., Rao M S., Tetrahedron 2004 60 2125
19. Srikrishna A, Pardeshi V H., Satyanarayana G, Tetrahedron: Asymmetry 2010 21 746
20. Srikrishna A, Pardeshi V H., Tetrahedron 2010 66 6810
21. Srikrishna A, Pardeshi V H., Mahesh K, Tetrahedron: Asymmetry 2010 21 2512
22. Srikrishna A, Pardeshi V H., Mahesh K, Tetrahedron: Asymmetry 2010 21 2830
23. Srikrishna A, Nagaraju G, Ravi G, Synlett 2010 3015
24. Srikrishna A, Nagaraju G, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011 50 73
25. Srikrishna A, Dethe D H., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011 50 1092
26. Srikrishna A, Seth V M., Nagaraju G, Synlett 2011 2343
27. Johnson W S., Werthemann L, Bartlett W R., Brocksom T J., Li T.-t, Faulkner D J., Petersen R, J. Am. Chem. Soc. 1970 92 741
28. Grubbs R H., Chang S, Tetrahedron 1998 54 4413
29. Fürstner A, Angew. Chem. Int. Ed. 2000 39 3013
30. Trnka T M., Grubbs R H., Acc. Chem. Res. 2001 34 18
31. Grubbs R H., Tetrahedron 2004 60 7117