Photochemical and thermal bergman cyclization of a pyrimidine enediynol and enediynone.
[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.
Choy
N
N
Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33124, USA.
Blanco
B
B
Wen
J
J
Krishan
A
A
Russell
K C
KC
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
D000970:Antineoplastic Agents; D004278:DNA, Superhelical; D053281:Enediynes; D011743:Pyrimidines; C418566:enediynol; C418567:enediynone