TY  - JOUR
A1  - Schmidt, Bernd
A1  - Hoelter, Frank
T1  - A stereodivergent synthesis of all stereoisomers of centrolobine : control of selectivity by a protecting-group manipulation
N2  - All stereoisomers of the natural product centrolobine are selectively synthesized, by starting from a common precursor. Key steps are an enantioselective allylation with enantiomerically pure allylsilanes, a tandem ring-closing metathesis-isomerization reaction, and a Heck reaction by using an arene diazonium salt. By choosing appropriate conditions for the final deprotection step, either the cis-configured centrolobines or their epimers are selectively obtained.
Y1  - 2009
UR  - http://www3.interscience.wiley.com/cgi-bin/jhome/26293/
U6  - https://doi.org/10.1002/chem.200902053
SN  - 0947-6539
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Elizarov, Nelli
A1  - Berger, René
A1  - Hoelter, Frank
T1  - Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes a protecting-group economic synthesis of phenolic stilbenes
JF  - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
N2  - 4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4'-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.
Y1  - 2013
U6  - https://doi.org/10.1039/c3ob40420j
SN  - 1477-0520
VL  - 11
IS  - 22
SP  - 3674
EP  - 3691
PB  - Royal Society of Chemistry
CY  - Cambridge
ER  -