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 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.
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2007 ◽
Vol 72
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pp. 7451-7454
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Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol
2015 ◽
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pp. 1934578X1501000
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pp. 4803-4815
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pp. 9926-9931
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pp. 10065-10075
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