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A Stereodivergent Synthesis of All Stereoisomers of Centrolobine: Control of Selectivity by a Protecting‐Group Manipulation
Author(s) -
Schmidt Bernd,
Hölter Frank
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902053
Subject(s) - epimer , chemistry , enantioselective synthesis , protecting group , metathesis , isomerization , selectivity , tandem , natural product , ring closing metathesis , stereochemistry , combinatorial chemistry , salt metathesis reaction , cascade reaction , functional group , salt (chemistry) , organic chemistry , catalysis , alkyl , polymer , materials science , composite material , polymerization
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.