Cascade reactions involving formal [2+2] thermal cycloadditions: Total synthesis of artochamins F, H, I, and J

Angewandte Chemie - International Edition

Volumn 46, Issue 39, 2007, Pages 7501-7505

  Nicolaou, K C ^a,b   Lister, Troy ^a,b   Denton, Ross M ^a,b   Gelin, Christine F ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cycloaddition; Domino reactions; Microwaves; Natural products; Total synthesis

Indexed keywords

DOMINO REACTIONS; NATURAL PRODUCTS; THERMAL CYCLOADDITION REACTION; TOTAL SYNTHESIS;

CYCLOADDITION; ELECTRONS; MICROWAVES; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

REACTION KINETICS;

ARTOCHAMIN F; ARTOCHAMIN H; ARTOCHAMIN I; ARTOCHAMIN J; BENZOPYRAN DERIVATIVE; CATECHOL DERIVATIVE; ORGANIC COMPOUND; POLYCYCLIC HYDROCARBON; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS; TEMPERATURE;

BENZOPYRANS; CATECHOLS; MICROWAVES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; POLYCYCLIC COMPOUNDS; STILBENES; TEMPERATURE;

EID: 35048814051     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702363     Document Type: Article

References (42)

1. C. Boonlaksiri, W. Oonanant, P. Kongsaeree, P. Kittakoop, M. Tanticharoen, Y. Thebtaranonth, Phytochemistry 2000, 54, 415-417.
2. C.-C. Chen, Y.-L. Huang, J.-C. Ou, J. Nat. Prod. 1993, 56, 1594-1597.
3. E. H. Hakim, Asnizar, Yurnawilis, N. Aimi, M. Kitajima, H. Takayama, Fitoterapia 2002, 73, 668-673.
4. M. R. Fernando, S. M. D. Nalinie Wickramasinghe, M. I. Thabrew, P. L. Ariyananda, E. H. Karunanayake, J. Ethnopharmacol. 1991, 31, 277-282.
5. Y. H. Wang, A. J. Hou, L. Chen, D. F. Chen, H. D. Sun, Q. S. Zhao, K. F. Bastow, Y. Nakanish, X. H. Wang, K. H. Lee, J. Nat. Prod. 2004, 67, 757-761.
6. Y. H. Wang, A. J. Hou, D. F. Chen, M. Weiller, A. Wendel, R. J. Staples, Eur. J. Org. Chem. 2006, 3457-3463.
7. For another notable example of racemic natural products, see the endiandric acids: isolation: a) W. M. Bandaranayake, J. E. Banfield, D. St. C. Black, J. Chem. Soc. Chem. Commun. 1980, 19, 902-903;
8. total synthesis: b) K. C. Nicolaou, N. A. Petasis, R. E. Zipkin, J. Uenishi, J. Am. Chem. Soc. 1982, 104, 5555-5557;
9. c) K. C. Nicolaou, N. A. Petasis, J. Uenishi, R. E. Zipkin, J. Am. Chem. Soc. 1982, 104, 5557-5558;
10. d) K. C. Nicolaou, R. E. Zipkin, N. A. Petasis, J. Am. Chem. Soc. 1982, 104, 5558-5560;
11. e) K. C. Nicolaou, N. A. Petasis, R. E. Zipkin, J. Am. Chem. Soc. 1982, 104, 5560-5562.
12. For related cyclobutane-forming reactions that involve a benzopyran and a prenyl group, see: a) M. Mondal, V. G. Puranik, N. P. Argade, J. Org. Chem. 2007, 72, 2068-2076;
13. for a related formal [2+2] cycloaddition reaction that involves an allylic cation and a benzopyran, see: b) A. V. Kurdyumov, R. P. Hsung, J. Am. Chem. Soc. 2006, 128, 6272-6273;
14. for recent examples of thermal [2+2] cycloaddition reactions between allenes and alkenes, see: c) H. Ohno, T. Mizutani, Y. Kadoh, A. Aso, K. Miyamura, N. Fujii, T. Tanaka, J. Org. Chem. 2007, 72, 4378-4389;
15. d) M. Murakami, T. Matsuda in Modern Allene Chemistry, Vol. 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 727-815.
16. P. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett 1998, 26-28.
17. This choice was made after a Wittig reaction produced a mixture of stilbenes (E/Z ca. 1:1). To the best of our knowledge, this is the first application of the Julia-Kocienski reaction to stilbene synthesis, and it is recommended by virtue of its efficiency and apparently higher selectivity. For an alternative approach to stilbenes, see: J. E. Robinson, R. J. K. Taylor, Chem. Commun. 2007, 1617-1619.
18. a) Q. Wang, Q. Huang, B. Chen, J. Lu, H. Wang, X. She, X. Pan, Angew. Chem. 2006, 118, 3733-3735;
19. Angew. Chem. Int. Ed. 2006, 45, 3651-3653.
20. J. D. Godfrey, Jr., R. H. Mueller, T. C. Sedergran, N. Soundararajan, V. Colandrea, Tetrahedron Lett. 1994, 35, 6405-6408.
21. CCDC-648446 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
22. A Discovery System model number 908005 was used.
23. TLC analysis indicated that the Claisen rearrangements proceed faster than cleavage of the Boc group or the formal cycloaddition. Given the fact that hydroxy groups must be liberated prior to formation of the cyclobutane, the sequence shown in Scheme 3 is proposed.
24. 3PO are currently underway and full details will be reported in due course.
25. 2 and vinyl CH protons.
26. a) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, Angew. Chem. 2000, 112, 750-755;
27. Angew. Chem. Int. Ed. 2000, 39, 734-739;
28. b) K. C. Nicolaou, G.-Q. Cao, J. A. Pfefferkorn, Angew. Chem. 2000, 112, 755-759;
29. Angew. Chem. Int. Ed. 2000, 39, 739-743;
30. c) K. C. Nicolaou, J. A. Pfefferkorn, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc. 2000, 122, 9939-9953.
31. 13C NMR spectra of natural artochamins F, H, I, and J for comparison purposes.
32. We consider the stepwise mechanism shown in Scheme 6 to be a more plausible alternative to that originally proposed, see Ref. [6].
33. We must also consider two further mechanistic alternatives for the microwave-promoted reactions. The first, and least probable, involves a [π2s + π2a] cycloaddition. The second involves a stepwise diradical mechanism in which formation of the five-membered ring precedes diradical recombination, see Ref. [8a]. Preliminary experiments with (E)- and (Z)-5 a indicate that the formal cycloaddition reaction is not stereospecific with respect to the alkene geometry. On the basis of this observation a stepwise radical mechanism, in which bond rotation occurs to some extent before recombination of the diradical, or the redox mechanism shown in Scheme 6 are currently favored. These possibilities are under investigation and full details will be disclosed in due course.
34. For selected reviews on cascade reactions, see: a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
35. Angew. Chem. Int. Ed. 2006, 45, 7134-7186;
36. b) K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 5, 551-564;
37. c) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
38. d) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
39. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
40. e) H. Pellissier, Tetrahedron 2006, 62, 1619-1665;
41. f) H. Pellissier, Tetrahedron 2006, 62, 2142-2173;
42. g) R. A. Bunce, Tetrahedron 1995, 51, 13103-13159.