Preparation of cis-4-O-protected-2-cyclopentenol derivatives

Details Preparation of cis-4-O-protected-2-cyclopentenol derivatives Preparation of cis-4-O-protected-2-cyclopentenol derivatives

1996-02-01

1998-03-17

Owens, Amelia

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568731, 556470, 556482, 549421, C07C 3506

Patent

active

057288992

ABSTRACT:
The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.

REFERENCES:
patent: 5244896 (1993-09-01), Borcherding et al.
C.R. Johnson, et al., J. Chem. Soc., Chem. Commun., 1139-1140 (1995).
S.M. Siddiqi, et al., Nucleosides & Nucleotides, 12(2)185-198, pp. 185-198, (1993).
Journal of the American Chemical Society, vol. 106, No. 6, 1750-1759 (1984).
Heterocycles, vol. 16, No. 4, 605-608 (1981).
Liebigs Annalen Der Chemie, No. 3, 195-200 (1991).
Tetrahedron, vol. 47, No. 36, 7569-7582, (1991).
Merlo, V., et al., J. Chem. Soc. Perkin Tans. 1, 1477 (1994).
Merlo, V., et al., J. Chem. Soc. Perkins Trans. 1, 1717, (1993).
H. C. Brown & P.M. Weissman, J. Am. Chem. Soc., 87(24), 5614 (1965).
K. Lauman & M. Schneider, Tetrahedron Lett. 25 (51), 5875 (1984).
Nokami, J., et al., Tetrahedron Lett., 32(21), 2409 (1991).
Harre, M., et al., Angew. Chem. Int. ed. Engl., 21, 480 (1982).
S. K. Hendrie & J.Leonard, Tetrahedron, 3289, (1987).
Corey, E.J., et al., Tetrahedron Lett., 27(20), 2199 (1986).
Nara, M., et al., Tetrahedron, 36, 3163 (1980).
Johnson C. R., et al., Tetrahedron Lett., 35(12), 1833 (1994).
M. Asami, Bull. Chem. Soc. Jpn., 63, 1402, (1990).
C. R. Johnson & S. J. Bis, Tetrahedron Lett., 33 (48), 7287 (1992).
M. Asami, Tetrahedron Lett., 26(47), 5803) (1985).

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