Intermediates for preparation of taxols

Details Intermediates for preparation of taxols Intermediates for preparation of taxols

1992-06-23

1993-12-28

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

052741370

ABSTRACT:
A taxol intermediate selected from the group consisting of: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each selected from hydrogen, hydroxyl, or a protected hydroxyl; or R.sup.1 and R.sup.2 together form an oxo or a protected oxo; R.sup.3 is formyl, a protected formyl, or --CH(X)--OY wherein X is hydrogen or a monovalent metal and Y is hydrogen or a hydroxyl protecting group; and R.sup.4 and R.sup.5 are different and each selected from chloro or cyano; or R.sup.4 and R.sup.5 together form an oxo or a protected oxo, with the proviso that R.sup.1 and R.sup.2 are not both hydroxyl; R.sup.6 is hydroxyl or a protected hydroxyl; R.sup.7 is hydrogen, hydroxyl, or a protected hydroxyl; R.sup.8 is carboxyl, hydroxylmethyl, or a protected hydroxylmethyl; or R.sup.7 and R.sup.8 when taken together with carbon atoms 3 and 4, form an oxetane ring; or R.sup.6 and R.sup.8 when taken together with carbon atoms 1 and 4, form a bridged lactone; R.sup.9 is hydrogen or a hydroxyl protecting group; R.sup. 10 is hydroxyl or a protected hydroxyl; or R.sup.8 and R.sup.10 when taken together with carbon atoms 4 and 5, form a .gamma.-butyrolactone ring; R.sup.11 is alkoxycarbonyl, formyl, a protected formyl, hydroxylmethyl or a protected hydroxylmethyl; or R.sup.6 and R.sup.11 when taken together with carbon atoms 1 and 6, form a 2,2-dimethyl-1,3-dioxane ring; and the dotted line between the 2- and 3-positions of the six-membered ring represents an optional bond.

REFERENCES:
A. S. Kende, et al., "Synthesis of a Taxane Triene," J. Am. Chem. Soc., (1986) 108, 3513-3515.
L. Pettersson, et al., "An Enantiospecific Synthesis of a Taxol A-Ring Building Unit," Tetrahedron Letters, vol. 28, No. 24, pp. 2753-2756, (1987).
Y. Ohtsuka, et al., "Synthesis of 3,8,11,11-Tetramethyl-4-oxobicyclo[5.3.1] undecane as a Model for Taxane Synthesis," Chem.Pharm.Bull., (1988,) 36, 4711-4721.
I. Kitagawa, et al., "Synthesis of a Chiral 1,1,3-Trimethylcyclohexane Derivative from d-Camphor . . . " Chem. Letters, (1980,) 1001-1004.
C. S. Swindell, "Taxane Diterpene Synthesis Strategies, A Review," Organic Preparations & Procedures, Int., (1991,) 23, 465-555.

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