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Total Synthesis of (±)‐Halomon by a Johnson–Claisen Rearrangement
Author(s) -
Schlama Thierry,
Baati Rachid,
Gouverneur Véronique,
Valleix Alain,
Falck John R.,
Mioskowski Charles
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980817)37:15<2085::aid-anie2085>3.0.co;2-j
Subject(s) - claisen rearrangement , alkene , bromine , chemistry , chlorine , total synthesis , carroll rearrangement , stereochemistry , organic chemistry , catalysis
The total synthesis of the polyhalogenated antitumour agent halomon ( 1 ) was accomplished with two novel transformations as key steps: a Johnson–Claisen rearrangement of a dichlorinated alkene for the preparation of the tertiary chlorinated C3 and a new rearrangement of bromohydrins for the regiospecific introduction of the bromine and chlorine atoms on C6 and C7, respectively.