Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd-0-Catalyzed Asymmetric C(sp(3))-H Activation

Melot, Romain; Craveiro, Marcus V.; Burgi, Thomas; Baudoin, Olivier

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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd-0-Catalyzed Asymmetric C(sp(3))-H Activation

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Author(s):	Melot, Romain ^[1] ; Craveiro, Marcus V. ^[1] ; Burgi, Thomas ^[2] ; Baudoin, Olivier ^[1] Total Authors: 4
Affiliation:	^[1] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel - Switzerland ^[2] Univ Geneva, Dept Phys Chem, 30 Quai Ernest Ansermet, CH-1211 Geneva 4 - Switzerland Total Affiliations: 2
Document type:	Journal article
Source:	ORGANIC LETTERS; v. 21, n. 3, p. 812-815, FEB 1 2019.
Web of Science Citations:	3
Abstract
A divergent enantioselective synthesis of (nor)-illudalane sesquiterpenes was designed by using a Pd-0-catalyzed asymmetric C(sp(3))-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. (AU)

FAPESP's process:	16/22636-2 - Total Synthesis of (R)-Puraquinonic Acid using Enantiosselective C(sp3)-H Activation
Grantee:	Marcus Vinicius Craveiro
Support Opportunities:	Scholarships abroad - Research

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