Concise total syntheses of variolin B and deoxyvariolin B.
The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.
Anderson
Regan J
RJ
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Hill
Jonathan B
JB
Morris
Jonathan C
JC
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
D001372:Aza Compounds; D011743:Pyrimidines; C474921:variolin B; D014269:Trifluoroacetic Acid; D010100:Oxygen