10.1021/jo1003746
The research focuses on the catalytic asymmetric total synthesis of platyphyllide, a norsesquiterpene lactone. The primary purpose of this study is to develop an efficient and enantioselective synthetic route to platyphyllide using a catalytic asymmetric Diels-Alder reaction, and to revise the absolute configuration of natural (-)-platyphyllide based on the synthesized compound. The key chemicals used in this research include Danishefsky diene, an electron-deficient alkene, Yb(OTf)3 as the central metal catalyst combined with axially chiral ligands (BINAMIDE or BINUREA), and various reagents for subsequent transformations such as Pd(OAc)2 for Ito-Saegusa oxidation and Grignard reagents. The study successfully synthesized platyphyllide through a series of reactions, including the Diels-Alder reaction to obtain a highly substituted cyclohexene derivative, followed by oxidation to a protected cyclohexane-1,3-dione, and further transformations to achieve the final product. The researchers discovered that the optical rotation of the synthesized platyphyllide was opposite to that of the natural compound, leading to the revision of the absolute configuration of natural (-)-platyphyllide to the (6S,7S)-enantiomer. This work not only provides a new synthetic method for platyphyllide but also clarifies its absolute stereochemistry through X-ray crystallographic analysis of a key intermediate.
10.1016/j.tetlet.2011.12.033
The research investigates the effectiveness of ytterbium triflate in catalyzing the Meerwein–Ponndorf–Verley (MPV) reduction of various substituted aromatic and aliphatic aldehydes and ketones using isopropanol as both the solvent and reducing agent. The study demonstrates that ytterbium triflate can efficiently promote this reduction process, yielding primary and secondary alcohols in yields ranging from 22% to 98%. The methodology involves dissolving the carbonyl compound and ytterbium triflate in isopropanol and stirring the mixture at reflux overnight. After solvent evaporation, catalyst recovery, and purification, the desired alcohols are obtained. Notably, the catalyst can be reused multiple times without significant loss of activity. The study concludes that ytterbium triflate offers a practical and environmentally friendly alternative for MPV reductions, with mild reaction conditions and satisfactory yields.