Formal Convergent Synthesis of Ivermectin Aglycone - A Synthetic Approach to the C10-C25 Subunit of Avermectins 2b

Abstract A convergent, two-fragment synthesis of the C10-C25 northern moiety of avermectins has been developed. Along with our previous work in this area, the present contribution represents a formal synthesis of Ivermectin aglycone. Furthermore, according to a strategy leading to non γ-pyranone add...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2009-10, Vol.2009 (20), p.3477-3487
Main Authors: Henryon, Vivien, Férézou, Jean-Pierre
Format: Article
Language:English
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Summary:Abstract A convergent, two-fragment synthesis of the C10-C25 northern moiety of avermectins has been developed. Along with our previous work in this area, the present contribution represents a formal synthesis of Ivermectin aglycone. Furthermore, according to a strategy leading to non γ-pyranone adducts from the condensation reaction between acetylacetone dianion and convenient aldehydes, 23-hydroxylated C10-C25 northern building blocks required for the synthesis of the avermectins series 2b were prepared. Subsequent unexpected kinetically favored unnatural (21S)-spiro isomers were obtained under mild cyclization conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1216954