483-26-1Relevant articles and documents
Rhodium-catalyzed hydrocarbonylation of a homoallylamine via n-h activation and application for synthesis of yohimbane alkaloids
Chiou, Wen-Hua,Wang, Yu-Wei,Kao, Chien-Lun,Chen, Po-Chou,Wu, Chen-Chang
, p. 4240 - 4244 (2014)
We describe syntheses of n-yohimbane and alloyohimbane using Rh-catalyzed hydrocarbonylation, which provides a practical methodology to synthesize a δ-lactam from a secondary homoallyl amine. We have also observed an unexpected transformation where the am
A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids
Miller, Eric R.,Hovey, M. Todd,Scheidt, Karl A.
, p. 2187 - 2192 (2020/02/04)
We report a concise, enantioselective synthesis of the yohimbine alkaloids (-)-rauwolscine and (-)-alloyohimbane. The key transformation involves a highly enantio- and diastereoselective NHC-catalyzed dimerization and an amidation/N-acyliminium ion cyclization sequence to furnish four of the five requisite rings and three of the five stereocenters in two operations. This route also provides efficient access to all four diastereomeric arrangements of the core stereotriad of the yohimbine alkaloids from a common intermediate. This platform approach in combination with the ability to access both enantiomers from the carbene-catalyzed reaction is a powerful strategy that can produce a wide range of complex alkaloids and related structures for future biomedical investigations.
Application of oxidative desymmetrization of meso-tetrahydrofurans: Syntheses of functionalized chiral building blocks and of (-)-alloyohimbane
Miyafuji, Akio,Ito, Katsuji,Katsuki, Tsutomu
, p. 261 - 272 (2007/10/03)
Oxidative desymmetrization of oxygen functionalized mesotetrahydrofurans was successfully achieved (up to 87% ee) through (salen)manganese(III) catalyzed enantiotopic selective C-H oxidation. The enantioselective synthesis of (-)-alloyohimbane (12) has also been achieved in a short step by using oxidative desymmetrization of meso-tetrahydrofuran as the key step.
