Process for the preparation of clausenamide and neoclausenamide,

Details Process for the preparation of clausenamide and neoclausenamide, Process for the preparation of clausenamide and neoclausenamide,

1990-08-13

1992-07-21

Springer, David B.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548534, C07D20726

Patent

active

051324334

ABSTRACT:
A process for the preparation of compound of the formula ##STR1## in which R.sup.1 --represents ##STR2## and R.sup.2 --represents hydrogen, fluorine, chlorine or bromine. Comprising cyclizing compounds of the formula ##STR3## and, in a further step, either a) reducing stereo-specifically to give compounds of the formula in which R.sup.1 represents ##STR4## or b), to give compounds of the formula in which R.sup.1 represents ##STR5## or by c) forming compounds of the formula ##STR6## followed by stereoselective reduction to give compounds in which R.sup.1 represents ##STR7##

REFERENCES:
Journal of the American Chemical Society, vol. 107, 1985, pp. 1438-1439; S. Hanessian et al.: "A New Synthetic Strategy for the Penemas, Total Synthesis of [5R,6S, 8R]-6-[Hydroxyethyl]-2-[Hydroxymethyl]Penem-3-Carboxylic Acid", p. 1439, left column, Compound 1.
Journal of Organic Chemistry, vol. 52, No. 19, Sep. 18, 1987, pp. 4352-4358; W. Hartwig, et al., "Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide".
Chemical Abstracts, vol. 106, No. 19, May 11, 1987, Columbus, Oh., USA, M. Yang et al.: "Isolation and Structural Elucidation of Clausenamide from the Leaves of Clausena Iansium [Lour.] Skeels" p. 401; ref. No. 153109Z & Yaoxue Xueboa 1987, 22[1], 33-40.

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