201002-22-4Relevant academic research and scientific papers
Rapid and enantioselective synthetic approaches to germanicol and other pentacyclic triterpenes
Surendra, Karavadhi,Corey
supporting information; experimental part, p. 8865 - 8869 (2009/02/03)
Two exceedingly short synthetic routes to the key intermediate 2 for the synthesis of the pentacyclic triterpene germanicol 1 have been developed. In the first, the (S)-epoxide of farnesyl bromide is transformed in just three steps to the tetracyclic intermediate 7, which is converted to chiral 2 by treatment with polyphosphoric acid. The second synthetic route to 2 involves the coupling of the (S)-epoxide 8 with vinyl iodide 9 to give 10 and two-stage acid-catalyzed cyclization of 10 to form 2. During the course of this work we have also discovered a very unusual intramolecular 1,5-proton shift from a carbocation to a C-C double bond. The details of the process have been confirmed by 2H-labeling experiments.
The application of a Shapiro reaction - Suzuki coupling sequence to the stereoselective synthesis of E-trisubstituted olefins
Corey,Roberts, Bryan E.
, p. 8919 - 8920 (2007/10/03)
A three-component coupling process is described for the rapid, stereoselective synthesis of a wide variety of E-trisubstituted olefins.
