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. Author manuscript; available in PMC: 2009 Jul 2.
Published in final edited form as: Science. 2008 May 2;320(5876):649–652. doi: 10.1126/science.1154690

Scheme 3.

Scheme 3

(a) H4N2 H2O (2 equiv.), AcOH (5 equiv.), MeOH, 25 °C, 45 min; (b) pyridine/DIPEA (9:1), 150 °C, 48 h; (c) Pb(OAc)4 (1.1 equiv.), CH2CI2, 0 °C, 30 min (43% of 9 from 2); (c') Pb(OAc)4 (1.2 equiv.), PhCH2COOH (50 equiv.) (premixed), CH2CI2, 0 °C, 30 min. (36% of 10 from 2); (d) hv (300 nm), EtOAc/benzene (1:1) or MeOH, 25 °C (67–92% for 3, 90% for 4)