%0 Journal Article
%A Melot, Romain
%A Craveiro, Marcus V.
%A Bürgi, Thomas
%A Baudoin, Olivier
%D 2019
%T Divergent Enantioselective Synthesis of (Nor)illudalane
Sesquiterpenes via Pd0‑Catalyzed Asymmetric C(sp3)–H Activation
%U https://acs.figshare.com/articles/journal_contribution/Divergent_Enantioselective_Synthesis_of_Nor_illudalane_Sesquiterpenes_via_Pd_sup_0_sup_Catalyzed_Asymmetric_C_sp_sup_3_sup_H_Activation/7579838
%R 10.1021/acs.orglett.8b04086.s001
%2 https://acs.figshare.com/ndownloader/files/14077742
%K chiral substrate
%K quaternary stereocenter
%K Divergent Enantioselective Synthesis
%K target molecules
%K Asymmetric
%K enantioenriched form
%K enantioselective synthesis
%K arylation
%K combination
%K Sesquiterpene
%K stereoselectivity
%K Catalyzed
%K Pd 0
%K deliquinone
%K approach
%K sesquiterpene
%K russujaponol
%K Activation
%K catalyst
%X A divergent enantioselective
synthesis of (nor)illudalane sesquiterpenes
was designed by using a Pd0-catalyzed asymmetric C(sp3)–H arylation as a key step to control the isolated,
highly symmetric quaternary stereocenter of the target molecules.
A matched combination of chiral substrate and catalyst proved optimal
to reach good levels of stereoselectivity. This approach enabled the
synthesis of three (nor)illudalanes, including (S)-deliquinone and (S)-russujaponol F, which are
synthesized for the first time in enantioenriched form.
%I ACS Publications