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An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...
EPFL2018
(-)-Quinocarcin (I) has been synthesized in a longest linear sequence of 22 steps from 3-hydroxybenzaldehyde in 16% overall yield. The Pictet-Spengler reaction of L-tert-butyl-2-bromo-5-hydroxy phenylalanate, synthesized according to Corey-Lygo's enantiose ...
The Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)-camphanate ((+)-(1R,2S,4R)-2-exo-cyano-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2- endo-yl (1'R)-camphanate ((+)-1)) was converted into (+)-2,7-dideoxy-2,4-di-C-methyl-L-glycero-((+)-6) and ...
In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...
At low temperature 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or Bronstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma -unsaturated silyl sulfinates can be desilylated and ...
From 2-cyano-6-phenyloxazolopiperidine, two highly efficient routes have been developed for the asym. synthesis of the spiropiperidine system: 1,8-diazaspiro[5.5]undecane. The key step was generation of the imine salts from the functionalized alpha -amino ...
1993
Zinc iodide‐catalyzed cycloaddition of furan to 1‐cyanovinyl (1′S)‐camphanate or 1‐cyanovinyl (1′R)‐camphanate led to optically pure (1R,2S,4R)‐2‐exo‐cyano‐7‐oxabicyclo[2.2.1]‐hept‐5‐en‐2‐yl (1S')‐camphanate and (1S,2R,4S)‐2‐exo‐cyano‐7‐oxabicyclo[2.2.1]he ...
Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)- or (1'S)-camphanate are transformed readily into polypropionate fragments containing four or five contiguous stereogenic centres. They can be condensed via cross-aldolizations to lit ...
Transition-metal catalyzed C-H functionalizations became a complementary and efficient bond-forming strategy over the past decade. In this respect, Cp*Rh(III) complexes have emerged as powerful catalysts for a broad spectrum of reactions giving access to s ...
