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Simple strategy for the synthesis of the avermectin-milbemycin family. Total synthesis of milbemycin .alpha.1

โœ Scribed by Hirama, Masahiro; Noda, Takeshi; Yasuda, Shohei; Ito, Sho


Book ID
127107353
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
385 KB
Volume
113
Category
Article
ISSN
0002-7863

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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 structurall

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The efficient synthesis of C-l to C-10 monocyclic nonaromatic fragments of the milbemycins and avermectins has been achieved, in which the key step involved the stereoselective addition of 2-lithio-4-phenylthiobut-1-ene to a 3-hydroxycyclohexanone derivative.