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. Author manuscript; available in PMC: 2014 Jan 25.
Published in final edited form as: J Am Chem Soc. 2012 Jul 25;134(31):13108–13113. doi: 10.1021/ja305342f

Table 1.

Diastereoselective Reduction of Aglain (±)-8a

graphic file with name nihms395901t1.jpg
entry reagenta solvent additive 9a:10ab yield (%)c
1 NaBH4 MeOH - - 0
2 NaBH4 THF - 1:5 93
3 Bu4NBH4 THF - 1:5 98
4 Me4NBH(OAc)3 benzene AcOH 3:1 95
5 Me4NBH(OAc)3 PhCF3 AcOH 5:1 95
6 NaBH(OAc)3 PhCF3 AcOH 10:1 95
a

See Supporting Information for detailed experimental procedures.

b

Determined by 1H NMR analysis of the crude reaction mixture.

c

Isolated after purification by silica gel chromatography.