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. Author manuscript; available in PMC: 2012 Dec 15.
Published in final edited form as: Bioorg Med Chem. 2011 Oct 19;19(24):7570–7581. doi: 10.1016/j.bmc.2011.10.034

Table 1.

HWE Condensations and subsequent hydrolysis.

graphic file with name nihms-337135-t0001.jpg

Entry RCHO R = HWE (% Yield) Stilbene Hydrolysis (% Yield) Schwein. R =
1 13 H 66% 43 53% 51 H
2 18 a Br 54% 44 a 92% 52 Br
3 25 F 53% 45 77% 53 F
4 31 SCH3 74% 46 40% 54 SCH3
5 40 CH2OCH3 50% 47 41% 55 CH2OCH3
6 41 OMOM 77% 48 61% 56 OH
7 42 OCH3 90% 49 92% 57 OCH3
8 34 CH2OTBS 36% 50
a

In this series, the aldehyde and stilbene bear a C-2 MOM group that is cleaved in the final hydrolysis.