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Beilstein J. Org. Chem. 2008, 4, No. 3, doi:10.1186/1860-5397-4-3
Graphical Abstract
Scheme 1: Donohoe's approach to (±)-1-epiaustraline utilising a modified Birch reduction.
Scheme 2: Reaction conditions i) Zn, HCl (aq).
Scheme 3: Reaction conditions: i) ref. [10] ii) ref. [11] iii) Zn, conc. HCl(aq).
Scheme 4: Potential mechanism for α-ketopyrrole reduction..
Scheme 5: Alternative reduction pathway.
Scheme 6: Catalytic hydrogenation.
Scheme 7: Reaction conditions: i) DIBAL-H, CH2Cl2, -78 °C, 1 h then triethylphosphonoacetate, NaH, THF, −78 °...
Scheme 8: i) ref. [17].
Scheme 9: i) CH3OH, Zn, conc. HCl(aq) ii) H2 (40 psi), Pd/C, EtOH, 2M HCl.