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. Author manuscript; available in PMC: 2010 May 21.
Published in final edited form as: Org Lett. 2009 May 21;11(10):2209–2212. doi: 10.1021/ol900594h

Table 1.

Stepwise Synthesis of Fused Tetrahydrofuransa

graphic file with name nihms-112056-t0006.jpg
entry R1 yield 15
(%)b 		yield 16
(%)b 		R2 yield 8
(%)b 		overall
yield (%)c
1 Ph 86 92 p-F3CPh 86 68
2 p-PhC(O)Ph 94 74
3 p-Tol 91 91 3-pyridyl 91 75
4 m-MeOPh 81 67
5 p-tBuPh 71 90 p-PhPh 87 43
6 2-naphthyl 85 54
7 p-PhC(O)Ph 44 92 (E)-β-styryl 67 27
8 6-MeO-2-naphthyl 89 36
a

Conditions: Steps 1 and 3: 1.0 equiv 11 or 16, 2.0 equiv ArBr, 2.0 equiv NaOtBu, 2 mol % Pd2(dba)3, 4 mol % Dpe-Phos, THF, 65 °C. Step 2: 1.0 equiv 15, 10 equiv TBAF, THF, rt.

b

Isolated yields (average of two or more experiments). All products were obtained with >20:1 dr.

c

Yield obtained over the three step sequence from 11 to 8.