A facile construction of the tricyclic 5-7-6 scaffold of fungi-derived diterpenoids. the first total synthesis of (±)-heptemerone G and a new approach to Danishefsky's intermediate for a guanacastepene A synthesis

Tetrahedron Letters

Volumn 51, Issue 33, 2010, Pages 4344-4346

  Michalak, Karol ^a   Michalak, Michał ^a   Wicha, Jerzy ^a  

^a POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Annulation reactions; Medium ring compounds; Quaternary stereocenters; Terpenoids; Total synthesis

Indexed keywords

DITERPENOID; GUANACASTEPENE A; HEPTEMERONE G; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COPRINUS; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY;

COPRINELLUS HEPTEMERUS; FUNGI;

EID: 77955421830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.064     Document Type: Article

References (39)

1. S. Brase, A. Encinas, J. Keck, and C.F. Nising Chem. Rev. 109 2009 3903 3990
2. L. Yet Chem. Rev. 100 2000 2963 3007
3. N.A. Petasis, and M.A. Patane Tetrahedron 48 1992 5757 5821
4. S.F. Brady, M.P. Singh, J.E. Janso, and S. Clardy J. Am. Chem. Soc. 122 2000 2116 2117
5. M.P. Singh, J.E. Janso, S.W. Luckman, S.F. Brady, J. Clardy, M. Greenstein, and W.M. Maiese J. Antibiot. 53 2000 256 261
6. C. Valdivia, M. Kettering, H. Anke, E. Thines, and O. Sterner Tetrahedron 61 2005 9527 9532
7. M. Kettering, C. Valdivia, O. Sterner, H. Anke, and E. Thines J. Antibiot. 58 2005 390 396
8. G.B. Dudley, and S.J. Danishefsky Org. Lett. 3 2001 2399 2402
9. D.S. Tan, G.B. Dudley, and S.J. Danishefsky Angew. Chem., Int. Ed. 41 2002 2185 2188
10. S.N. Lin, G.B. Dudley, D.S. Tan, and S.J. Danishefsky Angew. Chem., Int. Ed. 41 2002 2188 2191
11. M. Mandal, H.D. Yun, G.B. Dudley, S.N. Lin, D.S. Tan, and S.J. Danishefsky J. Org. Chem. 70 2005 10619 10637
12. W.D. Shipe, and E.J. Sorensen J. Am. Chem. Soc. 128 2006 7025 7035
13. F.D. Boyer, and I. Hanna Tetrahedron Lett. 43 2002 7469 7472
14. B. Shi, N.A. Hawryluk, and B.B. Snider J. Org. Chem. 68 2003 1030 1042
15. G. Mehta, K. Pallavi, and J.D. Umarye Chem. Commun. 2005 4456 4458
16. S. Iimura, L.E. Overman, R. Paulini, and A. Zakarian J. Am. Chem. Soc. 128 2006 13095 13101
17. A.K. Miller, C.C. Hughes, J.J. Kennedy-Smith, S.N. Gradl, and D. Trauner J. Am. Chem. Soc. 128 2006 17057 17062
18. X.J. Fang, and X.F. Tong Tetrahedron Lett. 51 2010 317 320
19. T. Hashimoto, Y. Naganawa, and K. Maruoka J. Am. Chem. Soc. 131 2009 6614 6617
20. C.K. Malik, and S. Ghosh Org. Lett. 9 2007 2537 2540
21. C.A. McGowan, A.K. Schmieder, L. Roberts, and M.F. Greaney Org. Biomol. Chem. 5 2007 1522 1524
22. S.V. Maifeld, and D. Lee Synlett 2006 1623 1644
23. K. Michalak, M. Michalak, and J. Wicha Tetrahedron Lett. 49 2008 6807 6809
24. K. Michalak, M. Michalak, and J. Wicha Molecules 10 2005 1084 1100
25. G. Mehta, J.D. Umarye, and K. Srinivas Tetrahedron Lett. 44 2003 4233 4237
26. E.W. Logusch Tetrahedron Lett. 20 1979 3365 3366
27. Y. Oikawa, T. Nishi, and O. Yonemitsu J. Chem. Soc., Perkin Trans. 1 1985 7 17
28. J. Attenburrow, A.F.B. Cameron, J.H. Chapman, R.M. Evans, B.A. Hems, A.B.A. Jansen, and T. Walker J. Chem. Soc. 1952 1094 1111
29. E.J. Corey, and N.W. Boaz Tetrahedron Lett. 26 1985 6019 6022
30. K.B. Sharpless, R.F. Lauer, and A.Y. Teranishi J. Am. Chem. Soc. 95 1973 6137 6139
31. H.J. Reich, J.M. Renga, and I.L. Reich J. Am. Chem. Soc. 97 1975 5434 5447
32. I. Ryu, S. Murai, I. Niwa, and N. Sonda Synthesis 1977 874 876
33. H. Wang, K. Michalak, M. Michalak, G. Jiménez-Osés, J. Wicha, and K.N. Houk J. Org. Chem. 75 2010 762 766
34. J.-L. Luche, L. Rodriguez-Hahn, and P. Crabbe Chem. Commun. 1978 601 602
35. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639 666
36. M.W. Rathke, and A. Lindert J. Am. Chem. Soc. 93 1971 2318 2320
37. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155 4156
38. A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, and G. Piancatelli J. Org. Chem. 62 1997 6974 6977
39. The spectra of compounds 2, 3, 4 and 23 are included in the Supplementary data.