Premium
A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β‐Hydroxy‐γ‐butyrolactone Intermediate
Author(s) -
Gade Narendar Reddy,
Iqbal Javed
Publication year - 2014
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.201402830
Subject(s) - chemistry , allylic rearrangement , intramolecular force , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a Pd II ‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers.