Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 6977-6980

  Snider, Barry B ^a   Chen, Jinsheng ^a   Patil, Ashok D ^b   Freyer, Alan J ^b  

^a BRANDEIS UNIVERSITY   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BATZELLADINE A; BATZELLADINE B; BATZELLADINE D; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01575-4     Document Type: Article

References (25)

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12. (c) Other studies: Murphy, P. J.; Williams, H. L.; Hurthouse, M. B.; Malik, K. M. A. J. Chem. Soc., Chem Commun. 1994, 119. Murphy, P. J.; Williams, H. L. J. Chem. Soc., Chem Commun. 1994, 819. Grillot, A. L.; Hart, D. J. Heterocycles 1994, 39, 435. Louwrier, S.; Ostendorf, M.; Tuynman, A.; Hiemstra, H. Tetrahedron Lett. 1996, 37, 905.
13. (c) Other studies: Murphy, P. J.; Williams, H. L.; Hurthouse, M. B.; Malik, K. M. A. J. Chem. Soc., Chem Commun. 1994, 119. Murphy, P. J.; Williams, H. L. J. Chem. Soc., Chem Commun. 1994, 819. Grillot, A. L.; Hart, D. J. Heterocycles 1994, 39, 435. Louwrier, S.; Ostendorf, M.; Tuynman, A.; Hiemstra, H. Tetrahedron Lett. 1996, 37, 905.
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20. 13C NMR 172.1, 150.7, 59.5, 58.0, 53.2, 52.0, 51.8, 49.8, 35.9, 34.5, 33.2, 30.9, 30.7 (2 C), 30.7, 30.6, 29.8, 26.4, 23.8, 18.9, 14.6.
21. 1H NMR spectrum of synthetic 3 indicates the presence of <5% of 15, which may be derived from 7b that formed tricyclic material without equilibration.
22. 12. Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805. Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, L; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007.
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24. 13. Molecular mechanics calculation were carried out using MODEL version KS 2.99 obtained from Prof. Kosta Steliou, Boston University.
25. 14. For another synthesis of 4 see: Franklin, A. S.; Overman, L. E. Presented at the 212th National Meeting of the American Chemical Society, Orlando, FL, August 1996.