Abstract
A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation-cyclization as the key steps.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Chemistry, Organic / methods*
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Copper / chemistry*
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Cyanides / chemistry*
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Cyclization
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Hydroxylation
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Isocoumarins / chemistry
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Lactones / chemical synthesis
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Lactones / chemistry*
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Polyketides / chemistry
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Stereoisomerism
Substances
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Cyanides
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Isocoumarins
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Lactones
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Polyketides
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Copper
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monocerin