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. Author manuscript; available in PMC: 2006 Apr 4.
Published in final edited form as: J Am Chem Soc. 2003 Dec 3;125(48):14702–14703. doi: 10.1021/ja0384734

Scheme 2a.

Scheme 2a

(a)p-MeOC6H4OH,DIAD,PPh3,THF,0°C,80%;(b)(CH2=CH)2CHOTBS, sBuLi, THF,-78 °C, then TBSOTf, 2,6-lutidine, -78 to 0 °C, 96%; (c) AD-mix-β, tBuOH/H2O, MeSO2NH2, 0 °C (3×), 70%; (d) noctylMgBr, CuCN, THF, -78 °C, 65%; (e)BiBr3, tBuMe2SiH, MeCN, 0°C, then 2,6-lutidine, TBSOTf, 0°C, 93%; (f) (NH4)2Ce(NO3)6, MeCN/H2O, -5°C, 91%.