Microwave-mediated nickel-catalyzed cyclotrimerization reactions: total synthesis of illudinine.
Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)(2)(PPh(3))(2) catalyst. This enables the facile construction of highly substituted indane, isoindoline, and tetraline core structures. The developed microwave-mediated Ni-catalyzed cyclotrimerization reaction was employed as the key step in a concise synthesis of the isoquinoline natural product illudinine. This represents the first example of a Ni-catalyzed cyclotrimerization reaction in total synthesis.
Teske
Jesse A
JA
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204,USA.
Deiters
Alexander
A
D002384:Catalysis; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry* / Q000528:radiation effects*; D009942:Organometallic Compounds / Q000737:chemistry* / Q000528:radiation effects*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D013237:Stereoisomerism
D009942:Organometallic Compounds; D012717:Sesquiterpenes; D009532:Nickel; C527341:illudinine