Background: (–)-Tatarinoids A, B, and C are 3 of 19 compounds that have been isolated from the rhizome
of the plant Acorus tatarinowii. Used in Chinese medicine, Acorus tatarinowii possesses pharmacological
effects on the central nervous system by regulating cyclic adenosine monophosphate (cAMP) activity. Previously
published computational studies suggested R configurations for all three natural products. No synthesis of (–)-
Tatarinoids A and B had been reported, while (–)- Tatarinoid C had been previously investigated and we have reported
on the first total synthesis of its enantiomer.
Objective: Herein, we describe the syntheses of (–)-Tatarinoids A, B, and C in 1 to 5 steps. Herein we also report
on how our synthetic studies of (–)-Tatarinoids A, B, and C allowed for structure elucidation and we revised the
stereochemical configurations of all three natural products.
Method: (–)-Tatarinoid A and (–)-Tatarinoid C are both constructed in 3 steps from 1-bromo-2,4,5-
Results: We have completed the syntheses of these natural products in overall yields of 63% and 74%, respectively
and in greater than 99% ee. (–)-Tatarinoid B is also synthesized from 1-bromo-2,4,5-trimethoxybenzene in
five steps with an overall yield of 11% and in greater than 99% ee.
Conclusion: We have concluded the correct stereochemical assignment for all three Tatarinoids is an S configuration
rather than the originally proposed R stereochemistry.