Premium
A Synthesis of (–)‐( R )‐ and (+)‐( S )‐Lavandulol, (+)‐Lavandulyl 2‐Methylbutanoate, and (+)‐Lavandulyl Senecioate through Orthoester Johnson–Claisen Rearrangement
Author(s) -
Fernandes Rodney A.,
Chowdhury Asim K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300520
Subject(s) - claisen rearrangement , chemistry , orthoester , carroll rearrangement , alcohol , cope rearrangement , stereochemistry , organic chemistry
An efficient synthesis of (–)‐( R )‐ and (+)‐( S )‐lavandulol, (+)‐lavandulyl 2‐methylbutanoate and (+)‐lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral‐pool approach to an allyl alcohol intermediate, and an orthoester Johnson–Claisen rearrangement as the key step.