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Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0‑Catalyzed Asymmetric C(sp3)–H Activation
journal contribution
posted on 2019-01-11, 20:14 authored by Romain Melot, Marcus V. Craveiro, Thomas Bürgi, Olivier BaudoinA 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.