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. Author manuscript; available in PMC: 2009 Jan 5.
Published in final edited form as: Org Lett. 2006 May 25;8(11):2353–2356. doi: 10.1021/ol0606435

Table 1.

Synthesis of N-Boc-O-TBS-Preussin Analogs

entry substrate ArBr product yield (%)
1 5 graphic file with name nihms-63796-t0007.jpg graphic file with name nihms-63796-t0008.jpg 70
2 12 graphic file with name nihms-63796-t0009.jpg graphic file with name nihms-63796-t0010.jpg 65
3 5 graphic file with name nihms-63796-t0011.jpg graphic file with name nihms-63796-t0012.jpg 52
4 12 graphic file with name nihms-63796-t0013.jpg graphic file with name nihms-63796-t0014.jpg 49
5 5 graphic file with name nihms-63796-t0015.jpg graphic file with name nihms-63796-t0016.jpg 69
6 12 graphic file with name nihms-63796-t0017.jpg graphic file with name nihms-63796-t0018.jpg 52
7 5 graphic file with name nihms-63796-t0019.jpg graphic file with name nihms-63796-t0020.jpg 69
8 5 graphic file with name nihms-63796-t0021.jpg graphic file with name nihms-63796-t0022.jpg 57
9 5 graphic file with name nihms-63796-t0023.jpg graphic file with name nihms-63796-t0024.jpg 62
10 5 graphic file with name nihms-63796-t0025.jpg graphic file with name nihms-63796-t0026.jpg 54
11 5 graphic file with name nihms-63796-t0027.jpg graphic file with name nihms-63796-t0028.jpg 40
12 5 graphic file with name nihms-63796-t0029.jpg graphic file with name nihms-63796-t0030.jpg 70

Conditions: 1.0 equiv substrate, 1.2 equiv ArBr, 2.3 equiv NaOtBu, 2 mol% Pd(OAc)2, 4 mol % dpe-phos, toluene, 90 °C.