Dipolar cycloaddition of rhodium-generated carbonyl ylides with p-quinones.
[reaction: see text] The dipolar cycloaddition of carbonyl ylides generated by the rhodium-catalyzed decomposition of delta- and epsilon-carbonyl-alpha-diazoketones with p-quinones leads to both C=O and C=C addition products. The product ratio is solvent- and catalyst-dependent and has been optimized to favor formation of either product. The C=C addition products of naphthoquinones are used in the assembly of structures hybridizing the illudin and anthraquinone anticancer agents.
Pirrung
M C
MC
Department of Chemistry, Levine Science Research Center, Duke University, Durham, North Carolina 27708-0317, USA. pirrung@chem.duke.edu
Kaliappan
K P
KP
D000903:Antibiotics, Antineoplastic / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D000081223:Polycyclic Sesquiterpenes; D011809:Quinones / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry; D012997:Solvents / Q000494:pharmacology; D013141:Spiro Compounds / Q000737:chemistry
D000903:Antibiotics, Antineoplastic; D000970:Antineoplastic Agents; D007659:Ketones; D000081223:Polycyclic Sesquiterpenes; D011809:Quinones; D012717:Sesquiterpenes; D012997:Solvents; D013141:Spiro Compounds; C410985:ptaquilosin; C052673:illudin M; D012238:Rhodium