731773-23-2Relevant academic research and scientific papers
Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A
Chaubet, Guilhem,Goh, Shermin S.,Mohammad, Mujahid,Gockel, Birgit,Cordonnier, Marie-Caroline A.,Baars, Hannah,Phillips, Andrew W.,Anderson, Edward A.
supporting information, p. 14080 - 14089 (2017/09/14)
Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium- and cobalt-catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component. A number of model systems were explored to investigate these two methodologies, and also to establish routes for the installation of the challenging benzopyran and butenolide rings.
Metal-catalyzed syntheses of abridged CDE rings of rubriflordilactones A and B
Goh, Shermin S.,Baars, Hannah,Gockel, Birgit,Anderson, Edward A.
, p. 6278 - 6281 (2013/02/23)
The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.
