Abstract
The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Cyclization
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Cyclohexane Monoterpenes
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Diterpenes / chemical synthesis
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Diterpenes / chemistry
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Ketones / chemistry*
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Molecular Structure
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Monoterpenes / chemical synthesis
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Monoterpenes / chemistry
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Pleuromutilins
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Polycyclic Compounds / chemistry*
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Stereoisomerism
Substances
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Anti-Bacterial Agents
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Biological Products
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Cyclohexane Monoterpenes
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Diterpenes
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Ketones
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Monoterpenes
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Polycyclic Compounds
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mutilin
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dihydrocarvone