Abstract
The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed by spiroacetalization.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclohexane Monoterpenes
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Molecular Structure
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Monoterpenes / chemical synthesis
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Monoterpenes / chemistry
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Sesterterpenes / chemical synthesis*
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Sesterterpenes / chemistry
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Stereoisomerism
Substances
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Cyclohexane Monoterpenes
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Monoterpenes
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Sesterterpenes
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Spiro Compounds
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alotaketal A
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carvone