Synthesis of Reactive Intermediates for Natural Cyclopentane Derivatives from (−)-Quinic Acid: Preparation of 11α-hydroxy-13-oxaprostanoic acid

Synthesis of Reactive Intermediates for Natural Cyclopentane Derivatives from (−)-Quinic Acid: Preparation of 11α-hydroxy-13-oxaprostanoic acid

We describe a flexible, stereocontrolled synthesis of enantiomerically pure substituted cyclopentenes and cyclopentanes ‐ including 11α‐hydroxy‐13‐oxaprostanoic acid 20 ‐ (−)‐quinic acid via an acyclic precursor 6 by an intramolecular aldolisation‐dehydration reaction.

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Veröffentlicht in:Helvetica chimica acta 1981-06, Vol.64 (4), p.1140-1144
Hauptverfasser: Barrière, Jean-Claude, Chiaroni, Angèle, Cléophax, Jeanine, Géro, Stephan D., Riche, Claude, Vuilhorgne, Mare
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe a flexible, stereocontrolled synthesis of enantiomerically pure substituted cyclopentenes and cyclopentanes ‐ including 11α‐hydroxy‐13‐oxaprostanoic acid 20 ‐ (−)‐quinic acid via an acyclic precursor 6 by an intramolecular aldolisation‐dehydration reaction.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19810640419