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Concise formal synthesis of (-)-(6R,11R,14R)-colletallol via D-proline catalysed α-aminooxylation-Wittig olefination strategy

By: Dey, Soumen.
Contributor(s): Gadakh, Sunita.
Publisher: New Delhi CSIR 2019Edition: Vol.58B(9), Sep.Description: 1029-1036p.Subject(s): GENERAL CHEMISTRYOnline resources: Click here In: Indian journal of chemistry (Section B)Summary: An efficient enantioselective formal synthesis of marine macrolide (−)-(6R,11R,14R)-colletallol has been achieved starting from commercially available raw materials. The key reactions include the D-proline catalyzed α-aminooxylation of aldehyde followed by Horner-Wardsworth-Emmons olefination in a sequential fashion to give the macrolide key intermediate 5 in high enantiomeric purity (97% ee) and high overall yield (32%).
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An efficient enantioselective formal synthesis of marine macrolide (−)-(6R,11R,14R)-colletallol has been achieved starting from commercially available raw materials. The key reactions include the D-proline catalyzed α-aminooxylation of aldehyde followed by Horner-Wardsworth-Emmons olefination in a sequential fashion to give the macrolide key intermediate 5 in high enantiomeric purity (97% ee) and high overall yield (32%).

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