Absolute stereostructure and total synthesis of leptomycin B

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8291-8294

  Kobayashi, Motomasa ^a   Wang, Weiqi ^a   Tsutsui, Yasuhiro ^a   Sugimoto, Masanori ^a   Murakami, Nobutoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Absolute stereostructure; Antitumor polyketide; Callystatin A; Leptomycin B; Streptomyces; Total synthesis

Indexed keywords

CALLYSTATIN A; LEPTOMYCIN B; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032487793     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01809-7     Document Type: Article

References (21)

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7. b) Fornerod, M.; Ohno, M.; Yoshida, M.; Mattaj, I. W. Cell, 1997, 90, 1051-1060.
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9. b) Murakami, N.; Wang, W.; Aoki, M.; Tsutsui, Y.; Higuchi, K.; Aoki, S.; Kobayashi, M. ibid., 1997, 38, 5533-5536.
10. c) Murakami, N.; Wang, W.; Aoki, M.; Tsutsui, Y.; Sugimoto, M.; Kobayashi, M. ibid., 1998, 39, 2349-2352.
11. 5. The physical data of authentic leptomycin B reported by Schaumberg, which we used for comparison, are a little different in chemical shifts and assignments from those reported in reference 1a. Schaumberg, J. P.; Hokanson, G. C.; French, J. C. J. Chem. Soc., Chem. Commun., 1984 1450-1452.
12. 6. a) Ley, S. V.; Armstrong, A.; Diez-Martin, D.; Ford, M. J.; Grice, P.; Knight, J. G.; Kolb, H. C.; Madin, A.; Marby, C. A.; Mukherjee, S.; Shaw, A. N.; Slawin, A. M. Z.; Vile, S.; White, A. D.; Williams, D. J.; Woods, M. J. Chem. Soc. Perkin Trans. I, 1991, 667-692.
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19. 3) δ: 6.94 (dd, J=9.7, 5.6 Hz, H-3), 6.65 (d, J=15.7 Hz, H-7), 6.01 (d, J=16.0 Hz, H-13), 6.00 (d, J=9.7 Hz, H-2), 5.71 (dd, J=15.7, 6.7 Hz, H-6), 5.59 (dt, J=16.0, 6.6 Hz, H-12), 5.41 (t, J=7.3 Hz, H-23), 5.23 (d, J=9.7 Hz, H-9), 5.09 (d, J=10.2 Hz, H-15), 5.00 (dd, J=7.0, 4.0 Hz, H-5), 4.15 (d, J=7.3 Hz, H-24), 3.64 (m, H-16), 3.58 (t-like, J =ca. 5, H-19).
20. 12. Dalcanale, E.; Montanari, F. J. Org. Chem., 1986, 51, 567-569.
21. 13. Synthetic 1: CD (McOH) λmax nm (Δeε): 300 (-22.4), 268 (0), 249 (+35.0), 229 (0), 222 (-3.4). Authentic leptomycin B: CD (MeOH): 300 (-22.4). 268 (0), 249 (+37.6), 229 (0), 222 (-3.4).