An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3, 3] Claisen Rearrangement. Issue 3 (30th January 2017)

• Record Type: Journal Article
• Authors: Bhosale, Viraj A.; Waghmode, Suresh B.
• Is Part Of: ChemistrySelect. Volume 2:Issue 3(2017)
• Page Start: 1262
• Page End: 1266
• Publication Date: 2017-01-30
• Subjects: Aminooxylation -- Claisen rearrangement -- Grignard Reaction -- Stereodivergent -- Wittig reaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201601890
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An efficient total synthesis of the enantiomerically pure lavandulol pheromones viz . (–)‐( R ) and (+)‐( S )‐lavandulol, (–)‐( R )‐lavandulyl acetate, (–)‐( R )‐lavandulyl propionate, (+)‐( S )‐lavandulyl 2‐methylbutanoate and (+)‐( S )‐lavandulyl senecioate is accomplished from nonchiral and chiral materials. The strategy utilizes a sequence of proline catalyzed asymmetric α‐aminooxylation and [3, 3] Claisen rearrangement for stereodivergent synthesis of chiral C‐2 unit containing 4‐pentenols. Abstract : Lavandulol pheromones and their derivatives have been efficiently synthesized from chiral C‐2 unit containing 4‐pentenol, which was accessed by using proline catalysed α‐aminooxylation and [3, 3] sigmatropic Claisen rearrangement of allyl vinyl ether as the key steps.