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

Barrière JeanClaude | Zendy; Chiaroni Angèle | Zendy; Cléophax Jeanine | Zendy; Géro Stephan D. | Zendy; Riche Claude | Zendy; Vuilhorgne Mare | Zendy

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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.

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