1027600-54-9Relevant academic research and scientific papers
Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine
Evans, Michael A.,Sacher, Joshua R.,Weinreb, Steven M.
experimental part, p. 6712 - 6719 (2011/02/26)
A strategy for a total synthesis of the marine alkaloid perophoramidine has been investigated. Key steps which have been tested include a tandem intramolecular Heck/carbonylation reaction and a stereoselective allylation of a pentacyclic δ-lactam to produ
Synthetic studies on perophoramidine and the communesins: Construction of the vicinal quaternary stereocenters
Seo, Jae Hong,Artman III, Gerald D.,Weinreb, Steven M.
, p. 8891 - 8900 (2007/10/03)
An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.
