Hydrogenation of gossypol catalyzed by supported noble metals. Issue 51 (17th December 2020)

• Record Type: Journal Article
• Authors: Täufer, Amely; Michalik, Dirk; Dinh Tien, Vu; Khac Vu, Tran; Vogt, Markus; Köckritz, Angela
• Is Part Of: Tetrahedron letters. Volume 61:Issue 51(2020)
• Publication Date: 2020-12-17
• Subjects: Gossypol -- Hydrogenation -- Heterogeneous catalysis -- Supported noble metal catalysts -- Axial chirality -- NMR; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152630
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The hydrogenation of atropisomeric gossypol to a new derivative gossoxol was carried out for the first time. The most active and selective catalyst was 5 wt% Rh/C. Plausible intermediates of the catalytic cycle were determined by tracking the hydrogenation using 1 H NMR spectroscopy. Abstract: The hydrogenation of gossypol using supported noble metal catalysts led to a new derivative named gossoxol in 5 to 69% yield. The most active and selective catalyst was 5 wt% Rh/C. The mechanism of the hydrogenation was discussed and plausible intermediates of the catalytic cycle were determined by tracking the behavior of gossypol in different solvents and at elevated temperature using 1 H NMR spectroscopy. The hydrogenation of anhydrogossypol also led to gossoxol, therefore it was regarded as an intermediate.