A stereodivergent synthesis of all stereoisomers of centrolobine: control of selectivity by a protecting-group manipulation.
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.
Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Strasse 24-25, 14476 Golm, Germany. bernd.schmidt@uni-potsdam.de
Bernd
B
Schmidt
Frank
F
Hölter
D003979:Diazonium Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D003979:Diazonium Compounds; D011714:Pyrans; C432457:centrolobin