2026-10-11T17:56:44Z https://api.figshare.com/v2/oai

oai:figshare.com:article/34027409 2026-09-29T19:11:34Z category_1 category_4 category_146 category_12 category_14 category_16 category_873 category_45 category_931 portal_63 item_type_6 month_year_09_2026

Enantioselective Formal Synthesis of (−)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation Jonathan Farhi (16294367) Brian M. Stoltz (1297560) Biophysics Biochemistry Space Science Cell Biology Molecular Biology Physiology Chemical Sciences not elsewhere classified Sociology Information Systems not elsewhere classified potentially general strategy initial approach employs densely functionalized α catalyzed reverse prenylation asymmetric deaminative cross enantioselective formal synthesis related oxaline alkaloids (−)- neoxaline enabled oxaline alkaloids asymmetric ir oxindole framework facile construction carboline framework archetypal member We report the enantioselective formal synthesis of neoxaline, an archetypal member of the oxaline alkaloids. An initial approach employs an asymmetric deaminative cross-coupling to install the 1,1-dimethylallyl (“reverse prenyl”) moiety onto an oxindole framework. Subsequent strategies employ iridium-catalyzed reverse prenylation onto tryptamine scaffolds, enabling the facile construction of a densely functionalized α-carboline framework. The route detailed herein represents a potentially general strategy for the synthesis of related oxaline alkaloids. 2026-09-29T00:00:00Z Text Journal contribution 10.1021/acs.joc.6c02094.s001 https://figshare.com/articles/journal_contribution/Enantioselective_Formal_Synthesis_of_-Neoxaline_Enabled_by_an_Asymmetric_Ir-Catalyzed_Reverse_Prenylation/34027409 CC BY-NC 4.0