Total synthesis of TK-57-164A, isariotin F, and their putative progenitor isariotin e

Angewandte Chemie - International Edition

Volumn 48, Issue 50, 2009, Pages 9519-9521

  Cha, Jacob Y ^a   Huang, Yaodong ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Blomimetic synthesis; Cyclization; Dearomatization; Resorcinol; Total synthesis

Indexed keywords

CHEMICAL EQUATIONS; DEAROMATIZATION; TOTAL SYNTHESIS;

PHENOLS;

CYCLIZATION;

BIOMIMETIC MATERIAL; EPOXIDE; FUSED HETEROCYCLIC RINGS; ISARIOTIN E; ISARIOTIN F; RESORCINOL; RESORCINOL DERIVATIVE; SPIRO COMPOUND; TK 57 164A; TK-57-164A;

ARTICLE; CYCLIZATION; METABOLISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; BIOMIMETIC MATERIALS; CYCLIZATION; EPOXY COMPOUNDS; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; METABOLIC NETWORKS AND PATHWAYS; RESORCINOLS; SPIRO COMPOUNDS;

EID: 73249127135     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904716     Document Type: Article

References (31)

1. a) J. Marco-Contelles M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2857-2900. For more recent examples, see:
2. b) IR. Haritakun, P. Srikitikulchai, P. Khoyaiklang, M. Isaka, J. Nat. Prod. 2007, 70,1478-1480
3. c) T. Amagata, K. Minoura, A. Numata,J. Nat. Prod. 2006, 69, 1384-1388
4. d) T. Amagata, M. Tanaka, T. Yamada, K. Minoura, A. Numata, J. Nat. Prod. 2008, 71, 340-345. For total syntheses of a related epoxide known, as scyphostatin, see:
5. e) M. Inoue, W. Yokota, M. G. Mlurugesh, T. Izuhara, T. Katoh, Angew. Chem. 2004, 776, 4303-4305;
6. Angew. Chem. Int. Ed. 2004, 43, 4207-4209
7. f) H. Fujioka, Y Sawama, N. Kotoku, T. Ohnaka, T. Okitsu, N. Murata, O. Kubo, R. Li, Y Kita, Chem. Eur. J. 2007, 75, 10225-10238
8. g) R. Takagi, W. Miyanaga, K. Tojo, S. Tsuyumine, K. Ohkata, J. Org. Chem.2007, 72, 4117-4125.
9. T. Bunyapaiboonsri, S. Yoiprommarat, K. Intereya, P. Rach-tawee, N. L. Hywel-Jones, M. Isaka, J. Nat. Prod. 2009, 72, 756-759.
10. A. Nakagawa, N. Nishikawa, S. Takahashi, K. Yamamoto, WO 2004-074269A1, 2004.
11. M. Tanaka, F. Nara, K. Suzuki-Konagai, T. Hosoya, T. Ogita, J. Am. Chem. Soc. 1997, 779, 7871-7872.
12. K. Murayama, T. Tanabe, Y. Ishikawa, K. Nakamura, S. Nishiyama, Tetrahedron Lett. 2009, 50, 3191-3194.
13. a) U. Schmidt, T. Beuttier, A. Lieberknecht, H. Griesser, Tetrahedron Lett. .1983, 24, 3573-3576
14. b) U. Schmidt, A. Lieberknecht, U. Schanbacher, T. Beuttler, J. Wild, Angew. Chem. 1982, 94, 191-198;
15. Angew. Chem. Int. Ed. Engl. 1982, 21, 770-777.
16. Commercially available, but for large scale preparation, see: a) U. Zoller, D. Ben-Ishai, Tetrahedron 1975, 57, 863-866
17. b) U. Schmidt, A. Lieberknecht, J. Wild, Synthesis 1984, 53-60.
18. a) T A. Wenderski, S. Huang, T. R. R. Pettus, J. Org. Chem. 2009, 74, 4104-4109
19. b) L. Mejorado, T. R. R. Pettus, J. Am. Chem. Soc. 2006, 128, 15625-15631
20. c) C. Hoarau, T. R. R. Pettus, Org. Lett. 2006, 8, 2843-2846
21. d) L. H. Pettus, R. W. Van De Water, T. R. R. Pettus, Org. Lett. 2001, 5, 905-908.
22. While superficially related to prior tyrosine dearomatizations that yield symmetric spirocyclic cyclohexadienone lactones demonstrated by P. Wipf, we are aware of only one other prior diastereoselective dearomatization yielding a dissymmetric spirocyclic cyclohexadienone lactone, see: G. Plourde, R. Spaetzel, J. S. Kwasnitza, TW. Scully, Molecules 2007, 12, 2215-2222.
23. a) D. J. Wardrop, M. S. Burge, W. Zhang, J. A. Ortiz, Tetrahedron Lett. 2003, 44, 2587-2591
24. b) D. J. Wardrop, M. S. Burge, J. Org. Chem. 2005, 70,10271-10284.
25. The initial dearomatization affords a separable 1.35:1.00 ratio of diastereomers which epimerizes to 12:1 upon, addition of DBN. A full account of dearomatization and epimerization studies will be reported in due course.
26. For a nice review of symmetric dienone reactivity see : a) P. Wipf, J.-K. Jung, Chem. Rev. 1999, 99, 1469-1480, and references cited therein. For examples of hydroxy-directed syn-epoxidation under anhydrous conditions, see:
27. b) W Adam, H. Kiliç, C. R. Saha-Mlöller, Synlett 2002, 510-512
28. c) K. Zilbeyaz, E. Sahin, H. Kiliç, Tetrahedron: Asymmetry 2007, 78, 791-796.
29. N. L. Burns, P. S. Baran, R. W Hoffmann, Angew. Chem. 2009, 121, 2896-2910;
30. Angew. Chem. Int. Ed. 2009, 48, 2854-2867.
31. D. Magdziak, S. J. Meek, T R. R. Pettus, Chem. Rev. 2004, 104, 1383-1429.