Total Synthesis
Our recently developed N,P-Iridium catalyzed asymmetric hydrogenations have found many useful applications in the total synthesis of natural molecules with important bioactivities.
Two examples that we reported in the past years were the total synthesis of (-)-Juvabione and Aliskiren. (ref 1-2)
In the Juvabiones synthesis, we used the asymmetric hydrogenation in one of the early steps of the synthesis and ,subsequently, we could also exploit the high regioselectivity of our N,P-Ir complex in the hydrogenation of 1,4-dienes to install the second stereocenter of the molecule and retain the other double bond. (ref 3)
The Aliskerin synthesis was achieved via a convergent total synthesis. We were able to prepare both the key intermediates of the synthesis using the high selectivity of N,P-Ir complexes in the hydrogenation of allylic alcohols.
We also developed a deoxygenation strategy that can be applied in the synthesis of Sertraline (a) and in the synthesis of a key intermediate for an important receptor ligand (b). (ref 4)
Recently, thanks to a very efficient KR of allylic alcohols, we also targeted the family of Inthomycin. We succeded in the synthesis of two late precursors for both the (3S)-Inthomycin A and (3S)-Inthomycin B. (ref 5)
1. J. Zheng, C. Margarita, S. Krajangsri, P. G. Andersson, Org. Lett., 2018, 20, 5676-5679
2. B.K. Peters, J. Liu, C. Margarita, P. G. Andersson, Chem. Eur. J., 2015, 21, 7292–7296
3. Peters, B. K.; Liu, J.; Margarita, C.; Rabten, W.; Kerdphon, S.; Orebom, A.; Morsch, T.; Andersson, P. G. J. Am. Chem. Soc. 2016, 138, 11930.
4. Zheng, J.; Jongcharoenkamol, J.; Peters, B. B. C.; Guhl, J.; Ponra, S.; Ahlquist M. S. G.; Andersson, P. G. Nature Catalysis 2019, 2, 1093–1100.
5. Wu, H.; Margarita C.; Jongcharoenkamol, J.; Nolan, M.; Singh, T.; Andersson, P. G. Chem. Sci. - Accepted Manuscript.