Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp(3))-H Activation Strategy

Author(s)

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

Affiliation

^[1] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel - Switzerland

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 84, n. 20, p. 12933-12945, OCT 18 2019.
• Web of Science Citations: 3

Abstract

Three (nor)illudalane sesquiterpenes were synthesized from a common intermediate in racemic and enantioenriched forms using Pd-0-catalyzed C(sp(3))-H arylation as a key step. The configuration of the isolated, highly symmetric quaternary stereocenter of the target molecules was controlled through a matched combination of chiral substrate and catalyst. Moreover, the recently developed Ir-catalyzed C-H borylation/Cu-catalyzed methylation method was employed to install the methyl group on the benzene ring. This strategy allowed the efficient synthesis of both racemic and (S)-configured puraquinonic acid, deliquinone, and russujaponol F. (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