Abstract
[reaction: see text] An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkanes / chemical synthesis*
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Alkanes / chemistry
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Alkanes / pharmacology
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Heterocyclic Compounds, 1-Ring / chemical synthesis*
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Heterocyclic Compounds, 1-Ring / chemistry
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Heterocyclic Compounds, 1-Ring / pharmacology
Substances
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Alkanes
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Antineoplastic Agents
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Heterocyclic Compounds, 1-Ring
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microcarpalide