Abstract
Krishnadimer A (1a), a C2-symmetric limonoid dimer representing a new class of axially chiral nonbiaryl natural products, was isolated and biomimetically semisynthesized by atroposelective 2,3-dichloro-5,6-dicyanobenzoquinone-mediated dienol-oxidative coupling. Single-crystal X-ray diffraction and electronic circular dichroism spectral analysis on the synthesized 1a unambiguously established its absolute configuration, including the P-configuration of the C15-C15' central axis. Antitumor investigations of the synthesized dimers 1a, 2a, and 2b revealed the large impact of axial chirality on bioactivities.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Benzoquinones / chemistry
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Biological Products / chemical synthesis*
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Biological Products / isolation & purification*
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Biomimetics
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Cell Line, Tumor
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Dimerization
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Drug Discovery
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Humans
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Limonins / chemical synthesis*
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Limonins / isolation & purification*
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Limonins / pharmacology
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Oxidative Coupling
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Stereoisomerism
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Tracheophyta / chemistry*
Substances
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Antineoplastic Agents
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Benzoquinones
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Biological Products
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Limonins
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quinone