Dispiroketals in synthesis. Part 23.1 A new
route to (+)-D-conduritol B from
myo-inositol
(Note: The full text of this document is currently only available in the PDF Version )
Jean E. Innes, Paul J. Edwards and Steven V. Ley
Abstract
Using
(2S,2′S)-2,2′-diphenyl-6,6′-bi(3,4-dihydro-2
H-pyran) to effect a simultaneous
protection–resolution of a myo-inositol
derivative, a new synthesis of
(+)-D-conduritol B has been
achieved.
References
Part 22: S. V. Ley, S. Mio and B. Meseguer, Synlett, 1996, 791 Search PubMed.
D. C. Billington, F. Perron-Sierra, I. Picard, S. Beaubras, J. Duhalt, J. Espinal and S. Challal, Bioorg. Med. Chem. Lett., 1994, 4, 2307 CrossRefCAS.
G. Legler, Methods Enzymol., 1977, 46, 368 CrossRefCAS.
G. Legler and M. Herrchen, FEBS Lett., 1981, 135, 139 CrossRefCAS.
G. Legler and R. Bollhagen, Carbohydr. Res., 1992, 233, 113 CrossRefCAS.
Z.-X. Guo, A. H. Haines, S. M. Pyke, S. G. Pyke and R. J. K. Taylor, Carbohydr. Res., 1994, 264, 147 CrossRefCAS.
See, for example;
(a) S. V. Ley, M. Parra, A. J. Redgrave and F. Sternfeld, Tetrahedron, 1990, 46, 4995 CrossRefCAS;
(b) T. Hudlicky, H. Luna, H. F. Olivio, C. Andersen, T. Nugent and J. D. Price, J. Chem. Soc., Perkin Trans. 1, 1991, 2907 RSC.
See, for example, R. Angelaud and Y. Landais, J. Org. Chem., 1996, 61, 5020 Search PubMed.
(a) H. Paulsen, W. Röben and F. R. Heiker, Chem. Ber., 1981, 114, 3342;
(b) C. Le Drain, J.-P. Vionnet and P. Vogel, Helv. Chim. Acta, 1990, 73, 161 CrossRef;
(c) T. Akiyama, H. Shima and S. Ozaki, Tetrahedron Lett., 1991, 32, 5593 CrossRefCAS;
(d) L. Yu, R. Cabrera, J. Ramirez, V. A. Malinovskii, K. Brew and P. G. Wang, Tetrahedron Lett., 1995, 36, 2897 CrossRefCAS;
(e) Two almost identical approaches; N. Chida, M. Ohtsuka, K. Nakazawa and S. Owaga, J. Chem. Soc., Chem. Commun., 1989, 436 Search PubMed; K.-I. Sato, M. Bokura and M. Taniguchi, Bull. Chem. Soc. Jpn., 1994, 67, 1633 RSC.
For a review of the synthesis and chemistry of dispiroketals, see S. V. Ley, R. Downham, P. J. Edwards, J. E. Innes and M. Woods, Contemp. Org. Synth., 1995, 365 Search PubMed.
N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793 CrossRefCAS and references cited therein.
C. Jiang and D. C. Baker, J. Carbohydr. Chem., 1986, 5, 615 CAS.
K. S. Bruzik and M.-D. Tsai, J. Am. Chem. Soc., 1992, 114, 6361 CrossRefCAS.
E. J. Corey and R. A. E. Winter, J. Am. Chem. Soc., 1963, 85, 2677 CrossRefCAS.
J. E. Innes,
Ph.D. Thesis, University of Cambridge,
1996.
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