The Catalytic Alkylative Desymmetrization of Anhydrides in a Formal Synthesis of Ionomycin

The catalytic desymmetrization of anhydrides with zinc reagents provides access to deoxypolypropionate and polypropionate synthons. A synthesis of ionomycin was pursued in which three of the four fragments were assembled using this methodology. Two of the strategies (enol silane/oxocarbenium couplin...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 50; no. 22; pp. 4343 - 4350
Main Authors Oberg, Kevin M., Cochran, Brian M., Cook, Matthew J., Rovis, Tomislav
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2018
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Summary:The catalytic desymmetrization of anhydrides with zinc reagents provides access to deoxypolypropionate and polypropionate synthons. A synthesis of ionomycin was pursued in which three of the four fragments were assembled using this methodology. Two of the strategies (enol silane/oxocarbenium coupling and reductive cyclization) were not successful at installing the C23 stereocenter, but this stereochemical issue was overcome through a reduction/SN2 approach. In addition to the synthesis of a protected diastereomer of ionomycin, the synthesis of a C17-C32 fragment constitutes a formal total synthesis.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610108