Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular‐Diels–Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)‐alpha‐Yohimbine. Issue 3 (12th June 2015)

• Record Type: Journal Article
• Authors: Feng, Wei; Jiang, Danfeng; Kee, Choon‐Wee; Liu, Hongjun; Tan, Choon‐Hong
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 3(2016)
• Page Start: 390
• Page End: 394
• Publication Date: 2015-06-12
• Subjects: alkaloids -- alkyne -- chiral guanidine -- intramolecular-Diels–Alder reaction -- total synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201500246
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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. Abstract : Tandem cycling : A bicyclic guanidine‐catalyzed asymmetric tandem isomerization intramolecular‐Diels–Alder reaction is reported to achieve the first catalytic enantioselective total synthesis of (+)‐alpha‐yohimbine.