Synthesis and NMR profiling of dioxabicyclo[3.2.1]octanes related to pinnatoxin D. Confirmation of the relative stereochemistry about rings E and F

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2621-2624

  Suthers, Bill D ^a   Jacobs, Mark F ^a   Kitching, William ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE; MARINE TOXIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TOXIN ANALYSIS; TOXIN SYNTHESIS;

EID: 0032559951     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00221-4     Document Type: Article

References (13)

1. 1. Uemura, D.; Chou, T.; Hains, T.; Nagatsu, A.; Fukuzawa, S.; Zhang, S. Chen, H. J.Am.Chem.Soc., 1995,117, 1155.
2. 2. Chou, T.; Kams, O.; Uemura, D. Tetrahedron Lett., 1996, 37, 4023.
3. 3. Chou, T.; Harris, T.; Kuramoto, H. Uemura, D. Tetrahedron Lett., 1996, 37, 4037.
4. 4. Sugimoto, T.; Ishihara, J.; Murai, A. Tetrahedron Lett., 1997, 38, 7379.
5. 5. Hu, T.; Curtis, J. M.; Oshima, Y.; Quilliam, M. A.; Walter, J. A.; Watson-Wright, W. M.; Wright, J. L. C. J.Chem.Soc.,Chem.Commun, 1995, 2159, and references therein. See also Jacobs, M. F.; Kitching, W. Current Organic Chemistry, 1998, 2(No.4), In Press.
6. 5. Hu, T.; Curtis, J. M.; Oshima, Y.; Quilliam, M. A.; Walter, J. A.; Watson-Wright, W. M.; Wright, J. L. C. J.Chem.Soc.,Chem.Commun, 1995, 2159, and references therein. See also Jacobs, M. F.; Kitching, W. Current Organic Chemistry, 1998, 2(No.4), In Press.
7. 6. Suthers, B.D.; Kitching, W. Unpublished Work.
8. 7. For molecules of this complexity containing C,H,O onfy, this approach would yield geometries and coupling constants very similar to those based on MM3 modelling, and valid for our purposes. The Assignment of H10" in 4 was confirmed by NOE observed across the ring from H7.
9. 8. Tu, Y. Q.; Moore, C. J.; Kitching, W. Tetrahedron: Asymmetry, 1995, 6(2), 397, and references therein.
10. 13C NMR data are located in Tables 1 and 2.
11. 10. See Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Tetrahedron Lett., 1986, 27, 3491.
12. 13C NMR data are located in Tables 1 and 2.
13. 6) δ 21.14(C14); 22.26(C13); 24.77(C4); 25,49(C10); 31.81(C9); 5.38(C3); 42.13(C11); 42.51(C5); 57.85(C8); 66.36(C12); 70.81(C2); 97.28(C6).