dafachronic-acid and methyl(trifluoromethyl)dioxirane

dafachronic-acid has been researched along with methyl(trifluoromethyl)dioxirane* in 1 studies

Other Studies

1 other study(ies) available for dafachronic-acid and methyl(trifluoromethyl)dioxirane

Article	Year
Site-selective and metal-free aliphatic C-H oxidation enabled synthesis of [5,24,25-D3]-(25S)-Δ(7)-dafachronic acid. Chemistry (Weinheim an der Bergstrasse, Germany), 2015, Mar-27, Volume: 21, Issue:14 Steroid hormones play significant roles in both worms and mammalians. (25S)-Δ(7)-Dafachronic acid (Δ(7)-DA, 1) is a member of the dafachronic acid hormonal series that regulates both development and lifespan of C. elegans. Despite its importance, effective tools for the illumination of its mode of action are lacking. Herein, we report an efficient synthesis of trideuterated Δ(7)-DA, [5,24,25-D3]-(25S)-Δ(7)-dafachronic acid ([D3]-Δ(7)-DA, 2), as a useful chemical tool for subsequent biological studies. Key steps for this bioinspired synthesis approach include site-selective aliphatic C-H oxidation mediated by methyl(trifluoromethyl)dioxirane (TFDO), and the iridium/phosphine-oxazoline-catalyzed late-stage asymmetric deuterium reduction. Topics: Animals; Catalysis; Cholestenes; Deuterium; Ethylene Oxide; Iridium; Oxidation-Reduction; Phosphines	2015

Article

Year

Site-selective and metal-free aliphatic C-H oxidation enabled synthesis of [5,24,25-D3]-(25S)-Δ(7)-dafachronic acid.

Chemistry (Weinheim an der Bergstrasse, Germany), 2015, Mar-27, Volume: 21, Issue:14

Steroid hormones play significant roles in both worms and mammalians. (25S)-Δ(7)-Dafachronic acid (Δ(7)-DA, 1) is a member of the dafachronic acid hormonal series that regulates both development and lifespan of C. elegans. Despite its importance, effective tools for the illumination of its mode of action are lacking. Herein, we report an efficient synthesis of trideuterated Δ(7)-DA, [5,24,25-D3]-(25S)-Δ(7)-dafachronic acid ([D3]-Δ(7)-DA, 2), as a useful chemical tool for subsequent biological studies. Key steps for this bioinspired synthesis approach include site-selective aliphatic C-H oxidation mediated by methyl(trifluoromethyl)dioxirane (TFDO), and the iridium/phosphine-oxazoline-catalyzed late-stage asymmetric deuterium reduction.

Topics: Animals; Catalysis; Cholestenes; Deuterium; Ethylene Oxide; Iridium; Oxidation-Reduction; Phosphines

2015