First total synthesis and stereochemical definition of isodomoic acid G.
[structure: see text] The first total synthesis and stereochemical definition of isodomoic acid G has been achieved. The key nickel-catalyzed coupling of an alkynyl enone with an alkenylzirconium allows formation of the pyrrolidine ring and most of the stereochemical features in a single step. This report provides the first total synthesis application of this new reaction and illustrates its utility in the stereoselective preparation of highly substituted 1,3-dienes.
D007608:Kainic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
D009942:Organometallic Compounds; D011759:Pyrrolidines; D015040:Zirconium; C032519:pyrrolidine; C012301:domoic acid; D007608:Kainic Acid