Skip to main content
. Author manuscript; available in PMC: 2016 Apr 15.
Published in final edited form as: Bioorg Med Chem. 2015 Feb 21;23(8):1849–1857. doi: 10.1016/j.bmc.2015.02.022

Table 3.

Functionalization of C6 (C7) alcohols

graphic file with name nihms666591u3.jpg
Entry R1 R2 Product Yield 1a Yield 2a
1 graphic file with name nihms666591t14.jpg H 27ab 57 –c
2 graphic file with name nihms666591t15.jpg H 27bb 43 62
3 graphic file with name nihms666591t16.jpg H 27cd 60 73
4 graphic file with name nihms666591t17.jpg H 27dd 83 76
5 graphic file with name nihms666591t18.jpg H 27ed 87 61
6 graphic file with name nihms666591t19.jpg Ac 27fe 86 38
7 graphic file with name nihms666591t20.jpg Piv 27gf 92 53
8 graphic file with name nihms666591t21.jpg graphic file with name nihms666591t22.jpg 27hf 76 72
a

Isolated yields.

b

X = OCH2CN; conditions: K2CO3, DMA, rt.

c

Only decomposition was observed.

d

X = Cl; conditions: 2,4,6-collidine, CH2Cl2, −78 °C to rt.

e

X = OAc; conditions: NEt3, DMAP (10 mol %), CH2Cl2, 0 °C–rt.

f

X = Cl; conditions: NEt3, DMAP (10mol%), CH2Cl2, 0°C–rt. See Supporting information for details on electrophile preparation.