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Synthesis of Reactive Intermediates for Natural Cyclopentane Derivatives from (−)‐Quinic Acid: Preparation of 11α‐hydroxy‐13‐oxaprostanoic acid
Author(s) -
Barrière JeanClaude,
Chiaroni Angèle,
Cléophax Jeanine,
Géro Stephan D.,
Riche Claude,
Vuilhorgne Mare
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640419
Subject(s) - chemistry , cyclopentane , cyclopentanes , quinic acid , intramolecular force , organic chemistry , dehydration , cyclohexanes , stereochemistry , catalysis , biochemistry
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.