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

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....

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2017-01, Vol.2 (3), p.1262-1266
Main Authors: Bhosale, Viraj A., Waghmode, Suresh B.
Format: Article
Language:English
Subjects:
Aminooxylation
Claisen rearrangement
Grignard Reaction
Stereodivergent
Wittig reaction
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Summary: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. 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.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201601890