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

Autor(es)

Melot, Romain ^[1] ; Craveiro, Marcus V. ^[1] ; Burgi, Thomas ^[2] ; Baudoin, Olivier ^[1]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 21, n. 3, p. 812-815, FEB 1 2019.
• Citações Web of Science: 3

Resumo

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)

• Processo FAPESP: 16/22636-2 - Síntese Total do ácido (R)-Puraquinônico através da Ativação C(sp3)-H Enantiosseletiva
• Beneficiário: Marcus Vinicius Craveiro
• Modalidade de apoio: Bolsas no Exterior - Pesquisa