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Total Synthesis of (-)-Platensimycin, a Novel Antibacterial Agent.
- Source :
-
Journal of Organic Chemistry . 2/6/2009, Vol. 74 Issue 3, p1163-1170. 8p. 9 Diagrams. - Publication Year :
- 2009
-
Abstract
- An enantioselective synthesis of platensimycin, a novel antibiotic natural product that inhibits bacterial β-ketoacyl-(acyl-carrier-protein) synthase (FabF), is described. Our synthetic strategy for the construction of the oxatetracyclic core involved an intramolecular Diels-Alder reaction. Our preliminary studies provided a complex tetracyclic product by first undergoing an interesting 1,5-hydride shift followed by a Diels-Alder reaction. Further optimization of the diene's electronic properties, by incorporation of a methoxy group, led to the oxatetracyclic core of platensimycin. The three required chiral centers, including two all-carbon quaternary chiral centers, were built in the intramolecular Diels-Alder step. The synthesis utilized natural (+)-carvone as the key chiral starting material, which determined the stereochemistry of the final product. The synthesis also featured an efficient Petasis olefination, a hydroboration sequence, a Gais's asymmetric Horner-Wadsworth-Emmons reaction, and a mercury salt catalyzed enol ether isomerization. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 74
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 36485139
- Full Text :
- https://doi.org/10.1021/jo802261f