Synthesis of the C17-C27 fragment of bryostatin 3

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7349-7352

  Obitsu, Tetsuo ^a   Ohmori, Ken ^a   Ogawa, Yasuyuki ^a   Hosomi, Hiroyuki ^a   Ohba, Shigeru ^a   Nishiyama, Shigeru ^a   Yamamura, Shosuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Biologically active compounds; Macrolides; Marine metabolites; Polyketides

Indexed keywords

ALDEHYDE DERIVATIVE; BRYOSTATIN; ESTER DERIVATIVE; GAMMA LACTONE DERIVATIVE; HALOGEN; HYDROXYL GROUP; IODINE DERIVATIVE; METAL; SILANE DERIVATIVE; VINYL DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG SYNTHESIS; HYDROLYSIS; OXIDATION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032192221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01577-9     Document Type: Article

References (19)

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2. b) Pettit, G. R. J. Nat. Prod. 1996, 59, 812-821.
3. 2. a) Norcross, R. D.; Paterson, I. Ghent. Rev. 1995, 95, 2041-2114. De Brabander, J.; Vandewalle, M. Pure Appl. Chem. 1996, 68, 715-718.
4. 2. a) Norcross, R. D.; Paterson, I. Ghent. Rev. 1995, 95, 2041-2114. De Brabander, J.; Vandewalle, M. Pure Appl. Chem. 1996, 68, 715-718.
5. c) Kalesse, M; Eh, M. Tetrahedron Lett. 1996, 37, 1767-1770.
6. d) Lampe, T. F. J.; Hoffmann, H. M. R. Tetrahedron Lett. 1996, 37, 7695-7698.
7. e) De Brabander, J.; Kulkarni, A.; Garcia-Lopez, R.; Vandewalle, M. Tetrahedron: Asymmetry 1997, 8, 1721 -1724.
8. f) Wender, P. A.; Brabander, J. D.; Harran, P. G.; Jimenez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C.-M. J. Am. Chem. Soc. 1998, 120, 4534-4535.
9. 3. a) Ohmori, K.; Suzuki, T.; Miyazawa, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1993, 34, 4981-4984.
10. b) Ohmori, K.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 6515-6518.
11. c) Ohmori, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 6519-6522.
12. 4. Parts of this study were presented at the Annual Meeting of the Chemical Society Japan (1997, 4G4 17; 1998, 4E7 02).
13. 4. Parts of this study were presented at the Annual Meeting of the Chemical Society Japan (1997, 4G4 17; 1998, 4E7 02).
14. 5. a) Schaufelberger, D. E.; Chmurny, G. N.; Beutler, J. A.; Koleck, M. P.; Alvarado, A. B.; Schaufelberger, B. W.; Muschik, G. M. J. Org. Chem. 1991, 56, 2895-2900.
15. b) Chmurny, G. N.; Koleck, M. P.; Hilton, B. D. J. Org. Chem. 1992, 57, 5260-5264.
16. 6. Essentially the same synthetic method as that for this compound has been published in ref. 3b.
17. -3, T=297 K. X-ray intensities were measured on a Rigaku AFC-5 diffractometer with Mo Kα radiation (γ= 0.71073 Å), and final R=0.060 for 3961 observed reflections. The details have been deposited at the Cambridge Crystallographic Data Center.
18. 3) -5.1, -4.6, -3.9, -3.7, 17.0, 18.5, 19.4, 23.0, 25.9, 26.3, 27.0, 27.4, 37.0, 46.8, 50.8, 61.0, 64.2, 71.4, 72.2, 75.7, 77.4, 77.6, 78.6, 103.4, 108.1, 127.9, 128.1, 128.3, 128.5, 128.6, 129.0, 130.1, 130.2, 132.6, 136.0, 138.9, 144.0.
19. 3) 0.92 (3H, t, J= 7.4 Hz), 1.19 (3H, d, J= 6.4 Hz), 1.26 (3H, s), 1.33 (3H, s), 1.30 -1.45 (2H, complex), 1.86 (1H, m), 2.01 (1H, m), 2.15 (1H, dd, J= 14, 7.2 Hz), 2.30 (1H, m), 3.37 (3H, s), 3.40 (1H, s), 3.57 (1H, s), 3.58 - 3.73 (3H, complex), 4.58 (1H, dd, J= 9.2, 1.6 Hz), 5.66 (1H, d, J= 15.6 Hz), 5.87 (1H, s), 6.06 (1H, d, J= 1.6 Hz), 6.09 - 6.19 (2H, complex), 7.13 (1H, m), 7.46 - 7.53 (3H, complex), 7.86 (2H, dd, J= 6.8, 1.6 Hz).