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Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine.
Feng, Wei; Jiang, Danfeng; Kee, Choon-Wee; Liu, Hongjun; Tan, Choon-Hong.
Affiliation
  • Feng W; Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
  • Jiang D; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Science, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
  • Kee CW; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Science, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371, Singapore.
  • Liu H; Key Laboratory of Natural Medicine and Immunoengineering of Henan Province, Henan University, Henan, 475004, China.
  • Tan CH; 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.
Chem Asian J ; 11(3): 390-4, 2016 Feb 04.
Article in En | MEDLINE | ID: mdl-25932622
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Yohimbine / Guanidine Language: En Journal: Chem Asian J Year: 2016 Document type: Article Affiliation country: Singapur
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Yohimbine / Guanidine Language: En Journal: Chem Asian J Year: 2016 Document type: Article Affiliation country: Singapur