Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305

Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305

A highly convergent, enantioselective synthesis of (+)-Sch 642305 is presented, which features a Mukaiyama−Michael addition followed by allylation to establish the syn−anti relationship of the three contiguous stereocenters. The 10-membered macrolactone was formed through ring-closing metathesis....

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Veröffentlicht in:Organic letters 2007-03, Vol.9 (7), p.1327-1329
Hauptverfasser: Wilson, Erica M, Trauner, Dirk
Format: Artikel
Sprache:eng
Schlagworte:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Cyclohexanones - chemistry
Cyclohexenes - chemistry
DNA Primase - antagonists & inhibitors
DNA, Bacterial - drug effects
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Macrolides - chemical synthesis
Macrolides - chemistry
Macrolides - pharmacology
Molecular Structure
Stereoisomerism
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Zusammenfassung:A highly convergent, enantioselective synthesis of (+)-Sch 642305 is presented, which features a Mukaiyama−Michael addition followed by allylation to establish the syn−anti relationship of the three contiguous stereocenters. The 10-membered macrolactone was formed through ring-closing metathesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070173u