Pd-catalyzed arylation reactions with phenol diazonium salts: application in the synthesis of diarylheptanoids

Bernd Schmidt; Frank Hölter; Alexandra Kelling; Uwe Schilde

doi:10.1021/jo2002787

Pd-catalyzed arylation reactions with phenol diazonium salts: application in the synthesis of diarylheptanoids

J Org Chem. 2011 May 6;76(9):3357-65. doi: 10.1021/jo2002787. Epub 2011 Apr 6.

Authors

Bernd Schmidt¹, Frank Hölter, Alexandra Kelling, Uwe Schilde

Affiliation

¹ Institut fuer Chemie (Organische Synthesechemie), Universitaet Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam-Golm, Germany. bernd.schmidt@uni-potsdam.de

PMID: 21434690
DOI: 10.1021/jo2002787

Abstract

The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biological Products / chemical synthesis
Biological Products / chemistry
Catalysis
Diarylheptanoids / chemical synthesis*
Diarylheptanoids / chemistry
Diazonium Compounds / chemistry*
Ethers, Cyclic / chemistry
Palladium / chemistry*
Phenol / chemistry*
Pyrans / chemical synthesis
Pyrans / chemistry
Stereoisomerism
Substrate Specificity

Substances

Biological Products
Diarylheptanoids
Diazonium Compounds
Ethers, Cyclic
Pyrans
centrolobin
Phenol
Palladium