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. Author manuscript; available in PMC: 2009 Dec 3.
Published in final edited form as: J Am Chem Soc. 2008 Dec 3;130(48):16190–16192. doi: 10.1021/ja807127s

Scheme 5. Completion of the Synthesisa.

Scheme 5

aConditions: (a) 3, 9-BBN, THF; then 2, DMF, H2O, 10 mol% PdCl2(dppf), 10 mol% Ph3As, Cs2CO3, 67% (b) 2-methyl-6-nitrobenzoic anhydride, 4-DMAP, DCE, 65% (c) HF·pyridine, pyridine, THF (d) Dess-Martin reagent, CH2Cl2 (e) DDQ, H2O, CH2Cl2 then dilute with 3:2 AcOH, H2O, 52% over 3 steps.