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. Author manuscript; available in PMC: 2009 Jan 8.
Published in final edited form as: J Am Chem Soc. 2006 Sep 13;128(36):11906–11915. doi: 10.1021/ja062364i

Scheme 7a.

Scheme 7a

a Reagents and conditions: (a) NaH, THF; n-BuLi; BOMCl (70%); (b) (R)-BINAP·RuBr2·Et3N (cat.), H2, MeOH (>99%); (c) TBSCl, imid, DMF (>99%); (d) DIBAL-H, PhMe, −78 °C (93%); (e) (+)-(ipc)2B(OMe), Z-MeCH=CHCH2Li (83%, 1:2, 61:62); (f) H2, Pd/C, MeOH (73%); (g) TPAP, NMO, CH2Cl2 (85%); (h) TBAF, THF (51%); (i) 64, Ph2SO, Tf2O, TBP, PhMe/CH2Cl2 (1:1); 62 (90%, 2:1, α: β); (j) H2, Pd/C, MeOH (94%); (k) RuCl3·H2O, NaIO4, H2O, MeCN (88%); (l) 2,4,6-Cl3C6H2COCl, Et3N, DMAP, CH2Cl2; add 62 (96%); (m) H2, Pd/C, MeOH (73%); (n) RuCl3·H2O, NaIO4, H2O, MeCN (96%).