Process for the preparation of clausenamide

Details Process for the preparation of clausenamide Process for the preparation of clausenamide

1986-10-03

1988-03-15

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548530, 548539, 548543, 548551, C07D20712

Patent

active

047314567

ABSTRACT:
A new synthetic route to clausenamide having the formula ##STR1## has been found. It has been found that a compound of the formula ##STR2## can be oxidized to provide the stereochemically correctly configured product, clasuenamide. A number of new compounds useful in the total synthesis of clausenamide have also been found. These compounds have the general formula ##STR3## wherein R is ##STR4## and CH.sub.2 OH.

REFERENCES:
Fieser, et al.; Reagents for Organic Synthesis, vol. 6, (1977), pp. 427-428; John Wiley & Sons, N.Y. and London.
Planta Medica, band 32, 1977, Stuttgart L. Mester et al., "Inhaltsstoffe aus Clausena anisata (Willd.) Oliv. (Rutaceae)I, Cumarine aus der Wurzelrinde" Seiten 81-85 *Seiten 81,81*.
Phytochemistry, Band 17, 1978, Oxford, New York, Frankfurt, Sydney Dhan Rakash et al., "Coumarins frm Clausena indica" Seiten 1194, 1195.
J. Chem. Soc., Chem. Commun., (1978), No. 7, pp. 281 to 282, Aboo Shoeb et al.
N. L. Drake and G. B. Cooke, Organic Syntheses, vol. 2, pp. 406-407.
Methoden Der Organischen Chemie, (Houben-Weyl), Band IV/ld, 1981, p. 267.
Methoden Der Organischen Chemie, (Houben-Weyl), Band VIII, 1952, p. 145.
Methoden Der Organischen Chemie, (Houben-Weyl), Band XIII/2a, 1973, pp. 289 to 294.
J. Chem. Soc., Chem. Commun., (1972), pp. 868 to 869, Brown, et al.
Reagents for Organic Synthesis, vol. 6, pp. 427 to 428, (1977) Freser, et al.
International Journal of Methods in Synthetic Organic Chemistry, Synthesis 1981, pp. 1 to 28, Mitsunobu.
International Journal of Methods in Synthetic Organic Chemistry, Synthesis, 1980, pp. 297 to 299.
Methoden Der Organischen Chemie, (Houben-Weyl), Band XIII/2a, 1973, pp. 302 to 312.

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