Total synthesis of rhazinilam: axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization.
A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.
Gu
Zhenhua
Z
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106, USA.
Zakarian
Armen
A
D000470:Alkaloids / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D054879:Halogenation; D007212:Indolizines / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis; D047028:Macrocyclic Compounds / Q000138:chemical synthesis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001688:Biological Products; D007212:Indolizines; D007769:Lactams; D047028:Macrocyclic Compounds; C009170:rhazinilam; D010165:Palladium
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