title: Photochemical and thermal bergman cyclization of a pyrimidine enediynol and enediynone.
abstract: [reaction: see text] Novel 10-membered pyrimidine enediynes (3 and 4) were synthesized in seven and eight steps, respectively. These compounds were compared for their abilities to undergo Bergman cyclization both thermally and photochemically. Alcohol 3 readily cyclized both thermally and photochemically in (i)PrOH, while ketone 4 only showed efficient thermal cyclization. Both compounds were also shown to cleave dsDNA under the appropriate conditions.
authors: Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33124, USA.
authors: N
authors: N
authors: Choy
authors: B
authors: B
authors: Blanco
authors: J
authors: J
authors: Wen
authors: A
authors: A
authors: Krishan
authors: K C
authors: KC
authors: Russell
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004278:DNA, Superhelical / Q000737:chemistry; D053281:Enediynes; D010777:Photochemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D004278:DNA, Superhelical; D053281:Enediynes; D011743:Pyrimidines; C418566:enediynol; C418567:enediynone