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

Bhosale Viraj A. | Zendy; Waghmode Suresh B. | Zendy

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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

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.

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