Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B

Angewandte Chemie - International Edition

Volumn 42, Issue 22, 2003, Pages 2528-2531

  Kodanko, Jeremy J ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Alkaloids; Asymmetric catalysis; C C coupling; Chiral resolution; Heck reactions

Indexed keywords

CATALYSIS; SYNTHESIS (CHEMICAL);

ALKALOIDS;

ORGANIC COMPOUNDS;

ALKALOID DERIVATIVE; HODGKINSINE; HODGKINSINE B; INDOLE DERIVATIVE; PYRROLIDINE DERIVATIVE; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALKALOIDS; INDOLES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 0038001590     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351261     Document Type: Article

References (37)

1. E. F. L. J. Anet, G. K. Hughes, E. Ritchie, Aust. J. Chem. 1961, 14, 173-174.
2. a) N. K. Hart, S. R. Johns, J. A. Lamberton, R. E. Summons, Aust. J. Chem. 1974, 27, 639-646;
3. b) F. Libot, C. Miet, N. Kunesch, J. E. Poisson, J. Pusset, T. Sévenet, J. Nat. Prod. 1987, 50, 468-473;
4. c) F. Guéritte-Voegelein, T. Sévenet, J. Pusset, M.-T. Adeline, B. Gillet, J. C. Beloeil, D. Guénard, P. Potier, J. Nat. Prod. 1992, 55, 923-930;
5. d) N. H. Lajis, Z. Mahmud, R. F. Toia, Planta Med. 1993, 59, 383-384;
6. e) L. Verotta, T. Pilati, M. Tatò, E. Elisabetsky, T. A. Amador, D. S. Nunes, J. Nat. Prod. 1998, 61, 392-396;
7. f) V. Jannic, F. Guéritte, O. Laprévote, L. Serani, M.-T. Martin, T. Sévenet, P. Potier, J. Nat. Prod. 1999, 62, 838-843.
8. L. Verotta, F. Orsini, M. Sbacchi, M. A. Scheildler, T. A. Amador, E. Elisabetsky, Bioorg. Med. Chem. 2002, 10, 2133-2142.
9. B. Robinson, Chem. Ind. 1963, 218-227.
10. J. B. Hendrickson, R. Göschke, R. Rees, Tetrahedron 1964, 20, 565-579.
11. a) J. Fridrichsons, M. F. Mackay, A. McL. Mathieson, Tetrahedron Lett. 1967, 3521-3524;
12. b) J. Fridrichsons, M. F. Mackay, A. McL. Mathieson, Tetrahedron 1973, 85-92.
13. For a recent review, see: U. Anthoni, C. Christophersen, P. H. Nielsen in Alkaloids: Chemical and Biological Perspectives, Vol. 13 (Ed.: S. W. Pelletier), Permagnon, New York, 1999, pp. 163-236.
14. T. A. Amador, L. Verotta, D. S. Nunes, E. Elisabetsky, Planta Med. 2000, 66, 770-772.
15. a) L, Verotta, F. Peterlongo, E. Elisabetsky, T. A. Amador, D. S. Nunes, J. Chromatogr. A 1999, 841, 165-176;
16. b) L. Verotta, personal communication to L. E. O., November 12, 2002.
17. a) M. Oestreich, P. R. Dennison, J. J. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485-1489; Angew. Chem. Int. Ed. 2001, 40, 1439-1442;
18. a) M. Oestreich, P. R. Dennison, J. J. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485-1489; Angew. Chem. Int. Ed. 2001, 40, 1439-1442;
19. b) A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer, M. M. Weiss, J. Am. Chem. Soc. 2003, 125, in press (ASAP Web release April 23, 2003).
20. For a recent review of the use of catalytic asymmetric intramolecular Heck reactions in the synthesis of natural products, see; L. E. Overman, A. B. Dounay, Chem. Rev. 2003, 103, in press.
21. A. D. Lebsack, J. T. Link, L. E. Overman, B. A. Stearns, J. Am. Chem. Soc. 2002, 124, 9008-9009.
22. a) J. T. Link, L. E. Overman, J. Am. Chem. Soc. 1996, 118, 8166-8167;
23. b) L. E. Overman, D. V. Paone, B. A. Stearns, J. Am. Chem. Soc. 1999, 121, 7702-7703;
24. c) L. E. Overman, J. F. Larrow, B. A. Stearns, J. M. Vance, Angew. Chem. 2000, 112, 219-221; Angew. Chem. Int. Ed. 2000, 39, 213-215.
25. c) L. E. Overman, J. F. Larrow, B. A. Stearns, J. M. Vance, Angew. Chem. 2000, 112, 219-221; Angew. Chem. Int. Ed. 2000, 39, 213-215.
26. H. Ishikawa, H. Takayama, N. Aimi, Tetrahedron Lett. 2002, 43, 5637-5639.
27. a) M. Iwao, T. Kuraishi, Org. Synth. 1996, 73, 85-93:
28. b) Approximately 1 equiv sBuLi apparently is tied up by complexation to one or more of the heteroatoms of 8. When 8 was treated with 1 equiv sBuLi, rac-9 was obtained in only 9% yield and 74% of 8 was recovered.
29. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629-635.
30. The cyclization of rac-7 failed when the following commercially available chiral ligands were used: -(+)-2-[2-(diphenylphosphanyl)phenyl-4-(1-methylethyl)-4,5-dihydrooxazole (Pfaltz ligand); (1S,2S)-(-)-1,2-diaminocyclohexane-N,N′-bis(2′diphenyl phosphanylbenzoyl) (Trost ligand).
31. a) Kindly provided by Professor Louisa Verotta.
32. b) L. Verotta unpublished results conveyed to L. E. O., January 14, 2003.
33. F. Libot, N. Kunesch, J. Poisson, M. Kaiser, H. Duddeck, Heterocycles 1988, 27, 2381-2386.
34. An earlier attempt by Shibasaki and co-workers to use an intramolecular Heck reaction to resolve a chiral intermediate produced only one of two possible diasteromers in measurable yield, see: S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Left. 1999, 40, 311-314.
35. L. E. Overman, E. A. Peterson, Angew. Chem. 2003, 115, 2629-2632; Angew. Chem. Int. Ed. 2003, 42, 2525-2528 (preceding communication in this issue).
36. L. E. Overman, E. A. Peterson, Angew. Chem. 2003, 115, 2629-2632; Angew. Chem. Int. Ed. 2003, 42, 2525-2528 (preceding communication in this issue).
37. S. B. Hoyt, L. E. Overman, Org. Lett. 2000, 2, 3241-3244.