Abstract
A new strategy featuring an iridium-catalyzed asymmetric hydrogenation of a racemic ketone via dynamic kinetic resolution to generate a cyclopentanol with three contiguous stereocenters and a SmI2-promoted pinacol coupling to install the six-membered ring with correct stereochemistry has been described for the enantioselective total synthesis of (-)-hamigeran B (19 steps, 10.6% overall yield) and (-)-4-bromohamigeran B (19 steps, 12.3% overall yield).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Catalysis
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Cyclopentanes / chemical synthesis
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Cyclopentanes / chemistry
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Hydrogenation
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Iridium / chemistry*
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Ketones / chemistry*
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Kinetics
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Molecular Structure
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Naphthoquinones / chemical synthesis*
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Naphthoquinones / chemistry
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Stereoisomerism
Substances
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4-bromohamigeran B
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Biological Products
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Cyclopentanes
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Ketones
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Naphthoquinones
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hamigeran B
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cyclopentanol
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Iridium