Biomimetic type approach to the tricyclic core of xyloketals. Application to a short, stereocontrolled synthesis of alboatrin and first synthesis of xyloketal G

Tetrahedron

Volumn 67, Issue 25, 2011, Pages 4559-4568

  Sarkar, Debayan ^a   Venkateswaran, Ramanathapuram V ^b  

^a Department of Chemistry   (India)

^b DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Alboatrin; Claisen rearrangement; Intra molecular cationic cyclization; Tandem ring opening and recylisation; Xyloketal G; Xyloketals

Indexed keywords

ACETAL; ALBOATRIN; LEWIS ACID; PLANT TOXIN; UNCLASSIFIED DRUG; XYLOKETAL G;

ACETYLATION; ARTICLE; BIOMIMETICS; CATALYSIS; CLAISEN REARRANGEMENT; CYCLIZATION; DEMETHYLATION; ISOMERIZATION; NONHUMAN; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 79957673675     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.084     Document Type: Article

References (30)

1. Y. Lin, X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, L.L.P. Vrijmoed, E.B.G. Jones, K. Krohn, K. Steingrover, and F. Zsila J. Org. Chem. 66 2001 6252 6256
2. J.W. Blunt, B.R. Copp, W.P. Hu, M.H.G. Munro, P.T. Northcote, and M.R. Prinsep Nat. Prod. Rep. 24 2007 31 86
3. W. Yin, Y. Lin, Z. She, L.L.P. Vrijmoed, and E.B.G. Jones Chem. Nat. Compd. 44 2008 3 5
4. F. Xu, Y. Zhang, J. Wang, J. Pang, C. Huang, X. Wu, Z. She, L.L.P. Vrijmoed, E.B.G. Jones, and Y. Lin J. Nat. Prod. 71 2008 1251 1253
5. X. Wu, X. Liu, G. Jiang, Y. Lin, W. Chan, and L.L.P. Vrijmoed Chem. Nat. Compd. 41 2005 27 29
6. X.Y. Wu, X.H. Liu, Y.C. Lin, J.H. Luo, Z.G. She, L. Houjin, W.L. Chan, S. Antus, T. Kurtan, B. Elsasser, and K. Krohn Eur. J. Org. Chem. 2005 4061 4064
7. J.D. Pettigrew, R.P. Freeman, and P.D. Wilson Can. J. Chem. 82 2004 1640 1648
8. K. Krohn, M. Riaz, and U. Flörke Eur. J. Org. Chem. 2004 1261 1270
9. J.D. Pettigrew, and P.D. Wilson Org. Lett. 8 2006 1427 1429
10. J.D. Pettigrew, and P.D. Wilson J. Org. Chem. 71 2006 1620 1625
11. J.D. Pettigrew, J.A. Cadieux, S.S.S. So, and P.D. Wilson Org. Lett. 7 2005 467 470
12. K. Krohn, and M. Riaz Tetrahedron Lett. 45 2004 293 294
13. S. Sabui, S. Ghosh, D. Sarkar, and R.V. Venkateswaran Tetrahedron Lett. 50 2009 4683 4684 and references cited therein
14. A. Ichihara, M. Nonaka, S. Sakamura, R. Sato, and A. Tajimi Chem. Lett. 1988 27 30
15. S.R. Graham, J.A. Murphy, and A.R. Kennedy J. Chem. Soc., Perkin Trans. 1 1999 3071 3073
16. R. Rodriguez, J. Mosses, A. Cowley, and J.E. Baldwin Org. Biomol. Chem. 3 2005 3488 3495
17. B. Biswas, D. Sarkar, and R.V. Venkateswaran Tetrahedron 64 2008 3212 3216
18. (Preliminary report) D. Sarkar, S. Ghosh, and R.V. Venkateswaran Tetrahedron Lett. 50 2009 1431 1434
19. S.N. Chavre, H. Choo, J.H. Cha, A.N. Pae, K. Choi II, and Y.S. Cho Org. Lett. 8 2006 3617 3619 and references cited therein
20. W.S. Johnson, L. Wethermann, W.R. Bartlett, T.J. Brockson, T. Li, D.J. Faulkner, and M.R. Peterson J. Am. Chem. Soc. 92 1970 741 743
21. T. Walenzyk, C. Carola, H. Buchholz, and B. Konig Tetrahedron 61 2005 7366 7377
22. A. Srikrishna, R. Viswajanani, J.A. Sattigeri, and C.V. Yelamaggad Tetrahedron Lett. 36 1995 2347 2350
23. S.P. Starkov, G.A. Goncharenko, M.N. Volkotrieb, and L.V. Zhidkova Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 36 1993 86 87
24. P.A. Bartlett Tetrahedron 36 1980 2 72
25. A.K. Ghosh, and D.K. Moon Org. Lett. 9 2007 2425 2427
26. Y. Fukuda, and Y. Okamoto Tetrahedron 58 2002 2513 2521
27. Y. Sugita, K. Kawai, and I. Yokoe Heterocycles 55 2001 135 144
28. Organic Syntheses, 1955; Collect. 3, 761; John Wiley and Sons, N.Y.
29. S. Venkateswarlu, G.K. Panchagnula, M.B. Guraiah, and G.V. Subbaraju Tetrahedron 61 2005 3013 3017
30. P.N. Preston, and T. Winwick J. Chem. Soc., Perkin Trans. 1 1983 1439 1441