Total synthesis of pseudopterosins
Final Report Abstract
In conclusion, we have developed a concise formal synthesis of the pseudopterosins, using a non-obvious transformation-based approach. We demonstrated that the key anionic oxy-Cope/transannular Michael cascade can be both efficient and remarkably selective, and therefore might prove useful in the stereocontrolled synthesis of other policyclic natural products. Although the selectivity in the key step was not quite in our favor, we obtained only 2 out of 16 possible diastereomers. Overall, this approach shortens the synthesis of phenol 5 from 13 to 8 steps. Based on Corey's report, the phenol 5 can converted to the pseudopterosin aglycon in 6 additional steps. As a result of the rapid synthesis of the spirocyclic cascade precursor and the efficiency of the key step, this total synthesis is highly compatible with state of the art syntheses by Sherburn and Luo.
Publications
- “Concise Formal Synthesis of the Pseudopterosins via Anionic OxyCope/Transannular Michael Addition Cascade” Org. Lett. 2020
Ramella, V.; Roosen, P. C.; Vanderwal, C. D.
(See online at https://doi.org/10.1021/acs.orglett.0c00486)
