1221498-99-2Relevant academic research and scientific papers
Evolution of a strategy for total synthesis of the marine fungal alkaloid (±)-communesin F
Seo, Jae Hong,Liu, Peng,Weinreb, Steven M.
experimental part, p. 2667 - 2680 (2010/06/20)
A new synthetic strategy for construction of the heptacyclic marine fungal alkaloid (±)-communesin F has been devised. Key reactions include an intramolecular Heck cyclization of a tetrasubstituted alkene to generate a tetracyclic enamide bearing one of the quaternary carbon centers (C7) of the alkaloid, an intramolecular reductive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containing the southern aminal, a stereoselective N-Boc-lactam enolate C-allylation to introduce the second quaternary carbon center (C8), and an azide reduction/N-Boc-lactam-opening cascade leading to the northern aminal.
Total synthesis of the polycyclic fungal metabolite (±)-communesin F
Liu, Peng,Seo, Jae Hong,Weinreb, Steven M.
supporting information; experimental part, p. 2000 - 2003 (2010/06/20)
(Chemical Equation Presented) What the Heck: The heptacyclic fungal alkaloid communesin F was the target of a total synthesis featuring a rare example of an intramolecular Heck cyclization of a tetrasubstituted alkene, a reductive cyclization of an N-Boc
