Squalestatin synthetic studies: tethered control in a bicycloketalisation step
(Note: The full text of this document is currently only available in the PDF Version )
Alison M. Reid and Patrick G. Steel
Abstract
A synthesis of an analogue of the dioxabicyclo[3.2.1]octane core structure of the squalestatins is reported in which control of the bicycloketalisation is achieved by a tethering strategy.
References
M. J. Dawson, J. E. Farthing, P. S. Marshall, R. F. Middleton, M. J. O'Neill, A. Shuttleworth, C. Stylli, R. M. Tait, P. M. Taylor, H. G. Wildman, A. D. Buss, D. Langley and M. V. Hayes, J. Antibiot., 1992, 45, 639 CAS.
C. Dufresne, K. E. Wilson, D. Zink, J. Smith, J. D. Bergstrom, M. Kurtz, D. Rew, M. Nallin, R. Jenkins, K. Bartizal, C. Trainor, G. Bills, M. Meinz, L. Y. Huang, J. Onishi, J. Milligan, M. Mojena and F. Pelaez, Tetrahedron, 1992, 48, 10 221 CrossRefCAS.
E. M. Carreira and J. Dubois, J. Am. Chem. Soc., 1994, 23, 10 825 CrossRef.
D. A. Evans, J. C. Barrow, J. L. Leighton, A. J. Robichaud and M. Sefkow, J. Am. Chem. Soc., 1994, 116, 12 111 CrossRefCAS.
K. C. Nicolaou, A. Nadin, J. E. Leresche, E. W. Yue and S. La Greca, Angew. Chem., Int. Ed. Engl., 1994, 21, 2190 CrossRef.
S. Caron, D. Stoermer, A. K. Mapp and C. H. Heathcock, J. Org. Chem., 1996, 61, 9126 CrossRefCAS; D. Stoermer, S. Caron and C. H. Heathcock, J. Org. Chem., 1996, 61, 9115 CrossRefCAS.
H. Sato, S. Nakamura, N. Watanabe and S. Hashimoto, Synlett, 1997, 451 CAS.
A. Armstrong, L. H. Jones and P. A. Barsanti, Tetrahedron Lett., 1998, 39, 3337 CrossRefCAS.
For a recent review see, A. Nadin and K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 1623 Search PubMed.
A. Armstrong and P. A. Barsanti, Synlett, 1995, 903 CrossRefCAS.
S. Caron, A. I. Mcdonald and C. H. Heathcock, J. Org. Chem., 1995, 60, 2780 CrossRefCAS.
S. G. Hegde and D. C. Myles, Tetrahedron, 1997, 53, 11 179 CrossRefCAS.
S. G. Hegde and D. C. Myles, Tetrahedron Lett., 1997, 38, 4329 CrossRefCAS.
D. Desmaële and J. d'Angelo, Tetrahedron Lett., 1989, 30, 345 CrossRefCAS.
O. Miyata and R. R. Schmidt, Tetrahedron Lett., 1982, 23, 1793 CrossRefCAS.
R. R. Schmidt and R. Hirsenkorn, Tetrahedron, 1983, 39, 2043 CrossRefCAS.
P. Bonete and C. Najera, Tetrahedron Lett., 1992, 33, 4065 CrossRefCAS.
G. E. Keck, D. E. Abbott and M. R. Wiley, Tetrahedron Lett., 1987, 28, 139 CrossRefCAS.
W. R. Roush, in
Comprehensive Organic Synthesis, ed.
B. M. Trost and I. Fleming,
Pergammon Press,
Oxford,
1991, vol. 2, ed.
C. H. Heathcock,
p. 1 Search PubMed.
I. Fleming, in
Comprehensive Organic Synthesis, ed.
B. M. Trost and I. Fleming,
Pergammon Press,
Oxford,
1991, vol. 2, ed.
C. H. Heathcock,
p. 563 Search PubMed.
G. E. Keck, S. Castellino and M. R. Wiley, J. Org. Chem., 1986, 51, 5478 CrossRefCAS.
V. J. Jephcote, A. J. Pratt and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1989, 1529 RSC.
P. Chan and J. M. Chong, Tetrahedron Lett., 1990, 31, 1985 CrossRefCAS.
C. H. Heathcock,
Material presented in RSC Centenary Lecture, Newcastle, November 1995,
1995 Search PubMed.
V. K. Aggarwal, M. F. Wang and A. Zaparucha, J. Chem. Soc., Chem. Commun., 1994, 87 RSC.
D. D. Perrin and
W. L. F. Armarego,
Purification of Laboratory Chemicals,
Pergammon Press,
Oxford,
1988 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.