Journal of Organic Chemistry 2005-08-05

Concise total syntheses of variolin B and deoxyvariolin B.

Regan J Anderson, Jonathan B Hill, Jonathan C Morris

Index: J. Org. Chem. 70(16) , 6204-12, (2005)

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Abstract

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.