Journal of the American Chemical Society, Vol.117, No.7, 1908-1939, 1995
Total Synthesis of the Antiparasitic Agent Avermectin B-1A
The synthesis of avermectin B-1a has been completed by a route that assembles the aglycon from three subunits consisting of the hexahydrobenzofuran moiety (A), the spiroketal segment (B), and the acyclic portion (C) comprising C9-C15. Connection is made in a B + C --> (B - C) + A sequence, and the synthesis is concluded by attachment to the aglycon of the L-oleandrosyl-L-oleandrose disaccharide via the pyridylthio glycoside.
Keywords:RADICAL CYCLIZATION APPROACH;HEXAHYDROBENZOFURAN SUBUNIT;ENANTIOSPECIFIC SYNTHESIS;3;4-DIHYDRO-2H-PYRAN APPROACH;STEREOCONTROLLED SYNTHESIS;MILBEMYCINS;(+)-MILBEMYCIN-BETA-3;CHEMISTRY;MACROLIDE;ROUTE