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Title

Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0-Catalyzed Asymmetric C(sp3)–H Activation

Authors
Melot, Romain
Craveiro, Marcus V.
Baudoin, Olivier
Published in Organic Letters. 2019, vol. 21, no. 3, p. 812-815
Abstract 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 et al. Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0-Catalyzed Asymmetric C(sp3)–H Activation. In: Organic Letters, 2019, vol. 21, n° 3, p. 812-815. doi: 10.1021/acs.orglett.8b04086 https://archive-ouverte.unige.ch/unige:141698

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Deposited on : 2020-09-22

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