466645-78-3Relevant academic research and scientific papers
Ruthenium catalyzed ring rearrangement: A rapid entry to substituted aza- and oxacycles
Ovaa, Huib,Stapper, Christian,Van Der Marel, Gijs A,Overkleeft, Hermen S,Van Boom, Jacques H,Blechert, Siegfried
, p. 7503 - 7518 (2002)
A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloh
Total synthesis of (+)-dihydrocuscohygrine and cuscohygrine
Stapper, Christian,Blechert, Siegfried
, p. 6456 - 6460 (2007/10/03)
The first enantioselective synthesis of (+)-dihydrocuscohygrine 1 and cuscohygrine 2 is presented. 1 was obtained in nine steps and 30% overall yield with a ruthenium-catalyzed tandem ring rearrangement metathesis key step starting from enantiomerically pure cycloheptene-1,3,5-triol derivative 6. The unknown absolute configuration of natural dihydrocuscohygrine 1 could be determined as (S,S)-(-). Cuscohygrine 2 was obtained by Jones oxidation of 1 in quantitative yield but unfortunately with complete epimerization.
