Skip to main content
. Author manuscript; available in PMC: 2016 Oct 2.
Published in final edited form as: J Org Chem. 2015 Oct 2;80(19):9740–9766. doi: 10.1021/acs.joc.5b01844

Scheme 12. Paspaline C Ring Construction and Synthesis of C6a Epimeric Ketonea.

Scheme 12

aReagents and conditions: (a) (i) HCl, H2O/MeOH/THF/acetone (10:10:10:1), 85 °C; (ii) DMP, CH2Cl2, rt; (b) vinylmagnesium bromide, CeCl3·2LiCl, THF, −78 °C; (c) Grubbs second generation catalyst (20 mol %), CH2Cl2, rt; (d) TFA, CH2Cl2, 0 °C to rt; (e) H2 (1 atm), Pd/C (1.50 mass equiv), EtOH, rt.