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. Author manuscript; available in PMC: 2014 Sep 2.
Published in final edited form as: J Med Chem. 2011 Mar 10;54(7):2266–2281. doi: 10.1021/jm1014296

Table 2.

Synthesis of 1-(2-Alkenyl)-bicyclo[3.3.0]oct-2-enes 18

R1 R2 R3 yield (%)a
18a Ph nHex Ph 86
18b Ph nHex 3-MeOPh 78
18c Ph nHex 4-MeOPh 72
18d Ph nHex 4-MePh 62
18e Ph nHex 4-EtPh 70
18f Ph nHex 4-nBuPh 78
18g Ph nHex 4-tBuPh 51
18h Ph nHex 4-PhPh 60
18i Ph nHex nPr 54
18j Ph nHex nBu 75
18k Ph nHex nHex 65
18l Ph nHex nOct 56
18m 3-MeOPh nHex Ph 75
18n 4-EtPh nHex Ph 70
18o nPr nHex Ph 82
18p nBu nHex Ph 88
18q nHex nHex Ph 86
18r cHex nHex Ph 80
18s (CH2)3OH nHex Ph 61
18t Ph H Ph 58
18u Ph nBu Ph 71
18v Ph nOct Ph 73
18w Ph SiMe2Ph Ph 45
a

Isolated yield of >95% pure material.