Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine.
Hydroisoquinoline derivatives were prepared in moderate to good enantioselectivities via a bicyclic guanidine-catalyzed tandem isomerization intramolecular-Diels-Alder (IMDA) reaction of alkynes. With this synthetic method, the first enantioselective synthesis of (+)-alpha-yohimbine was completed in 9 steps from the IMDA products.
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
Wei
W
Feng
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Science, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
Danfeng
D
Jiang
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Science, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
Choon-Wee
CW
Kee
Key Laboratory of Natural Medicine and Immunoengineering of Henan Province, Henan University, Henan, 475004, China.
Hongjun
H
Liu
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Science, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore. choonhong@ntu.edu.sg.
Choon-Hong
CH
Tan
D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D019791:Guanidine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D015016:Yohimbine / Q000138:chemical synthesis* / Q000737:chemistry
D015016:Yohimbine; D019791:Guanidine
alkaloids; alkyne; chiral guanidine; intramolecular-Diels-Alder reaction; total synthesis