Alexander Matzuk | Researchain

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Bioorganic & Medicinal Chemistry Letters | 1995

4 -DEOXY-4 -AMINOAVERMECTINS WITH POTENT BROAD SPECTRUM ANTIPARASITIC ACTIVITIES

Helmut Mrozik; Philip Eskola; Byron H. Arison; Bruce O. Linn; Aino Lusi; Alexander Matzuk; Thomas L. Shih; Maureen Tischler; Frank S. Waksmunski; Matthew J. Wyvratt; Timothy A. Blizzard; Gaye Margiatto; Michael H. Fisher; Wesley L. Shoop; John R. Egerton

Abstract Reductive amination of 4″-oxo-5-O-tert-butyldimethylsilyl-avermectins with sodium cyanoborohydride and ammonium acetate gave an epimeric mixture of 4″-deoxy-4″-amino analogs with the epimeric, axial 4″-β-amino derivative as the major component. Acylation of the amino substituent gave highly active broad spectrum antiparasitic compounds, as determined in a sheep anthelmintic assay. 4″-Epi-acetylamino-4″-deoxyavermectin B 1 ( 12 ) was selected for further antiparasitic studies and is currently under development as a novel avermectin endectocide.

Tetrahedron Letters | 1983

Synthesis of milbemycins from avermectins

Helmut Mrozik; John C. Chabala; Philip Eskola; Alexander Matzuk; Frank S. Waksmunski; Mary F. Woods; Michael H. Fisher

The structure of the avermectins and the milbemycins were interrelated by the conversion of 22,23-dihydroavermectin B1a and B1b aglycones (4) into 13-deoxy-22,23-dihydroavermectin B1a aglycone (9) and 13-deoxy-22,23-dihydroavermectin B1b aglycone (11) corresponding to 26-ethyl milbemycin-α3 and milbemycin B-41D respectively via reduction of the protected 13-chloroaglycone derivatives.

Journal of Medicinal Chemistry | 1964