Abstract
The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction of the β-side chain and aldol condensation. Clavulolactones II and III were successfully prepared from (S)-4-((tert-butyldimethylsilyl)oxy) cyclopent-2-en-1-one over nine steps, in overall yields of 21 and 7% respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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4-Butyrolactone / analogs & derivatives*
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4-Butyrolactone / chemical synthesis
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4-Butyrolactone / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Chemistry Techniques, Synthetic
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Cyclopentanes / chemical synthesis*
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Cyclopentanes / chemistry
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Oceans and Seas*
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Prostaglandins / chemical synthesis*
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Prostaglandins / chemistry
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Stereoisomerism
Substances
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Biological Products
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Cyclopentanes
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Prostaglandins
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4-Butyrolactone
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cyclopentenone