Abstract
A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric δ-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Alkenes / chemical synthesis*
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Alkenes / chemistry
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Amides / chemical synthesis*
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Amides / chemistry
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Molecular Structure
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Myxococcales / chemistry
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Organometallic Compounds / chemistry*
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Stereoisomerism
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Tin / chemistry*
Substances
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Aldehydes
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Alkenes
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Amides
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Organometallic Compounds
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crocacin C
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Tin