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. 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 13. Substrate-Directed Control of the C6a Stereocenter and Completion of the Total Synthesis of Paspalinea.

Scheme 13

aReagents and conditions: (a) LiAlH4, THF, 0 °C; (b) H2 (1 atm), C8H12IrP(C6H11)3C5H5N]PF6 (15 mol %), CH2Cl2, rt; (c) DMP, CH2Cl2, rt; (d) (i) LDA, THF, 0 °C, then HMPA, Me2S2; (ii) Nchloroaniline, CH2Cl2, −78 °C, then NEt3; (iii) Raney Ni, EtOH, rt; (iv) TsOH (66 mol %), CH2Cl2, 50 °C.