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Regioselective Cross‐Coupling Reactions as an Entry into Biologically Relevant Bithiazoles: First Total Synthesis of Cystothiazole E
Author(s) -
Bach Thorsten,
Heuser Stefan
Publication year - 2001
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 - 10.1002/1521-3773(20010903)40:17<3184::aid-anie3184>3.0.co;2-7
Subject(s) - regioselectivity , yield (engineering) , coupling reaction , coupling (piping) , chemistry , combinatorial chemistry , computational chemistry , stereochemistry , catalysis , organic chemistry , materials science , metallurgy
No problems have been encountered while using bithiazoles in Pd‐catalyzed cross‐coupling reactions. It was thus possible to achieve the first synthesis of cystothiazole E ( 1 ) with a Suzuki coupling of the building blocks 2 and 3 as the pivotal C−C bond‐formation step (94 % yield, TBDMS= t BuMe 2 Si). The bithiazole 3 could be prepared very conveniently from 2,4‐dibromothiazole by regioselective cross‐coupling reactions.