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Studies directed toward the total synthesis of the milbemycins: Synthesis of the C11 to C31 fragment of milbemycin D

✍ Scribed by Michael T. Crimmins; W.Gary Hollis Jr.; Danute M. Bankaitis-Davis

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 287 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96346-9

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✦ Synopsis

A highly stereocontrolled synthesis of the Cl 1 to C3 1 fragment of the potent antimicrobial agent milbemycin D has been completed.

This approach utilizes a unique hydrolysis-cyclization to construct the spiroketal portion of the molecule.

The milbemycins 2 and the avermectins3 are two structurally related classes of macrocyclic lactones with remarkable biological activity .4 These compounds show potent, broad spectrum anthelmintic, insecticidal, and acaracidal activity. Ivermectin, a semisynthetic derivative, is currently being employed as a veterinary medicine5 and is being used to treat onchocerciasis ("river blindness") in humans on an experimental basis.6

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