Total Synthesis of the Proposed Structure of Uncarialin A

The stereoselective total synthesis of the proposed structure of a potent serotonin 5-HT1A receptor agonist uncarialin A (1) is described. By employing the readily available meroquinene tert-butyl ester as the chiral synthon, the target structure has been prepared in a six-step linear sequence with a 17% overall yield. In comparison to the sample isolated from natural sources, the synthetic product shows significant spectral differences, strongly suggesting that the structure of the natural product should be revised.

Automated summary

The stereoselective total synthesis of a proposed potent serotonin 5-HT1A receptor agonist uncarialin A was achieved with a 17% overall yield using meroquinene tert-butyl ester as the chiral synthon. Spectral differences between the synthetic product and the sample isolated from natural sources suggest a need to revise the structure of the natural product.