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. Author manuscript; available in PMC: 2012 Dec 7.
Published in final edited form as: Chemistry. 2011 Jul 19;17(35):9777–9788. doi: 10.1002/chem.201002930

Table 1.

Deoxygenation Studies for Compounds 17 and 20

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Entry X Conditions Product Yield
1 H 10 mol% Rh2(OAc)4, C6H6, 80 °C 21 15%
2 H 10 mol% Rh2(OAc)4, C6H5CI, 80 °C 21 trace
3 H Al/HgCI2, C6H6/i-PrOH, reflux 21 + double bond isomer clean reaction
4 H WCI6, 3 equiv. n-BuLi, −78 °C → RT baseline material 0%
5 H (PhO)3PCH3I, BF3•OEt2, RT recovered 17 0%
6 TES 10 mol% Rh2(OAc)4, C6H6, 80 °C 18 52%