Intermediates for the production of epipodophyllotoxin and relat

Details Intermediates for the production of epipodophyllotoxin and relat Intermediates for the production of epipodophyllotoxin and relat

1988-09-16

1989-09-12

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

560 56, 560107, 560227, 560228, 560255, C07D31770, C07C 6975

Patent

active

048661899

ABSTRACT:
There is provided a novel and efficient stereoselective total synthesis of epipodoplyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)-alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.

REFERENCES:
patent: 3524844 (1988-08-01), Keller-Juslen et al.
patent: 4294763 (1981-10-01), Kende et al.
patent: 4391982 (1983-07-01), Kende et al.
W. J. Gensler & C. D. Gatsonis, J. Org. Chem., 31, 4004-4008 (1966).
W. J. Gensler, et al., J. Am. Chem. Soc., 82, 1714-1727 (1960).
A. S. Kende, et al., J. Org. Chem., 46, 2826-2828 (1981).
W. S. Murphy and S. Wattanasin, J. C. S. Perkin I, 271-276 (1982).
D. Rajapaksa, J. Am. Chem. Soc., 103, 6208-6209 (1981).
R. Rodrigo, J. Org. Chem., 45, 4538-4540 (1980).

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