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An Efficient Total Synthesis of (–)‐( R ), (+)‐( S )‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement
Author(s) -
Bhosale Viraj A.,
Waghmode Suresh B.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601890
Subject(s) - claisen rearrangement , propionate , proline , sex pheromone , stereochemistry , enantioselective synthesis , catalysis , chemistry , pheromone , organic chemistry , biology , amino acid , biochemistry , botany
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.