Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin

Journal of Organic Chemistry

Volumn 74, Issue 18, 2009, Pages 6924-6928

  Abdel Ghani, Sherif B ^a   Chapman, James M ^b   Figadére, Bruno ^c   Herniman, Julie M ^d   Langley, G John ^d   Niemann, Scott ^e   Brown, Richard C D ^d  

^a Ain Shams University   (Egypt)

^b ROCKHURST UNIVERSITY   (United States)

^c CNRS   (France)

^d UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^e CSS Analytical Co   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL HPLC; DIASTEREOISOMERS; FRAGMENT IONS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MIXTURES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ISOMERS;

ANNONA MURICATA EXTRACT; NATURAL PRODUCT; RETICULATACIN; UNCLASSIFIED DRUG; UVARIAMICIN I;

ANNONA MURICATA; ANNONACEAE; ARTICLE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NOMENCLATURE; PLANT ROOT; STEREOCHEMISTRY; SYNTHESIS;

ANNONA; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOLOGICAL PRODUCTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FURANS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 70249143306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9012578     Document Type: Article

References (24)

1. Reviews of the chemistry and biology of Annonaceous acetogenins: (a) Bermejo, A.; Figadère, B.; Zafra-Polo, M. C.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269-303.
2. (b) Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
3. (c) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z. M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306.
4. (d) Zafra-Polo, M. C.; Figadere, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117.
5. (e) Saez, J.; Sahpaz, S.; Villaescusa, L.; Hocquemiller, R.; Cavé, A.; Cortes, D. J. Nat. Prod. 1993, 56, 351-356.
6. (f) Rupprecht, J. K.; Hui, Y. H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
7. (a) Yu, J. G.; Hu, X. F. E.; Ho, D. K.; Bean, M. F.; Stephens, R. E.; Cassady, J. M.; Brinen, L. S.; Clardy, J. J. Org. Chem. 1994, 59, 1598-1599.
8. (b) Pettit, G. R.; Cragg, G. M.; Polonsky, J.; Herald, D. L.; Goswami, A.; Smith, C. R.; Moretti, C.; Schmidt, J. M.; Weisleder, D. Can. J. Chem.-Rev. Can. Chim. 1987, 65, 1433-1435.
9. Analysis of relative stereochemistry by NMR: (a) Hoye, T. R.; Suhadolnik, J. C. J. Am. Chem. Soc. 1987, 109, 4403-4404.
10. (b) Hoye, T. R.; Zhuang, Z. P. J. Org. Chem. 1988, 53, 5578-5580.
11. (c) Born, L.; Lieb, F.; Lorentzen, J. P.; Moeschler, H.; Nonfon, M.; Sollner, R.; Wendisch, D. Planta Med. 1990, 56, 312-316.
12. (d) Fujimoto, Y.; Murasaki, C.; Shimada, H.; Nishioka, S.; Kakinuma, K.; Singh, S.; Singh, M.; Gupta, Y. K.; Sahai, M. Chem. Pharm. Bull. 1994, 42, 1175-1184.
13. Application of Mosher's ester derivatives of Annonaceous acetogenins: (a) Rieser, M. J.; Hui, Y. H.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z. P.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10203-10213.
14. (b) Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nature Protoc. 2007, 2, 2451-2458.
15. Curran, D. P.; Zhang, Q. S.; Lu, H. J.; Gudipati, V. J. Am. Chem. Soc. 2006, 128, 9943-9956.
16. (a) Cecil, A. R. L.; Hu, Y.; Vicent, M. J.; Duncan, R.; Brown, R. C. D. J. Org. Chem. 2004, 69, 3368-3374.
17. (b) Hu, Y. L.; Cecil, A. R. L.; Frank, X.; Gleye, C.; Figadere, B.; Brown, R. C. D. Org. Biomol. Chem. 2006, 4, 1217-1219.
18. Gleye, C.; Duret, P.; Laurens, A.; Hocquemiller, R.; Cavé, A. J. Nat. Prod. 1998, 61, 576-579.
19. The diastereoisomers were separated for characterization, then recombined.
20. Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739-7743.
21. Exclusive formation of the desired butenolide has been reported for a very similar substrate: Goksel, H.; Stark, C. B. W. Org. Lett. 2006, 8, 3433-3436.
22. 13CNMRdata are compared in the Supporting Information.
23. See the Supporting Information for copies of HPLC chromatograms.
24. The results were further supported by collecting fractions from the chiral HPLC and analyzing the individual fractions using APCI MS (see the Supporting Information).