Divergent Enantioselective Synthesis of (Nor)illudalane
Sesquiterpenes via Pd0‑Catalyzed Asymmetric C(sp3)–H Activation
Posted on 2019-01-11 - 20:14
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.
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Melot, Romain; Craveiro, Marcus V.; Bürgi, Thomas; Baudoin, Olivier (2019). Divergent Enantioselective Synthesis of (Nor)illudalane
Sesquiterpenes via Pd0‑Catalyzed Asymmetric C(sp3)–H Activation. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b04086
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AUTHORS (4)
RM
Romain Melot
MC
Marcus V. Craveiro
TB
Thomas Bürgi
OB
Olivier Baudoin