Enantioselective Total Synthesis and Absolute Configuration of Apiosporic Acid

The first total synthesis of the polyketide apiosporic acid is presented. Key steps are a Julia–Kocienski olefination, a Suzuki–Miyaura cross-coupling, and an intramolecular Diels–Alder reaction. The absolute configuration of the natural product was determined.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2012-05, Vol.77 (9), p.4491-4495
Hauptverfasser:	Gärtner, Martin, Kossler, David, Pflästerer, Daniel, Helmchen, Günter
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Condensed benzenic and aromatic compounds Cross-Linking Reagents - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Structure Organic chemistry Polyketides - chemical synthesis Polyketides - chemistry Preparations and properties Stereoisomerism
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Beschreibung
Zusammenfassung:	The first total synthesis of the polyketide apiosporic acid is presented. Key steps are a Julia–Kocienski olefination, a Suzuki–Miyaura cross-coupling, and an intramolecular Diels–Alder reaction. The absolute configuration of the natural product was determined.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo300519g