et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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BnO<br />
PPTS<br />
OMe<br />
MeOH, CH 2Cl 2<br />
87 % two steps<br />
1. Ac 2O, py,<br />
DMAP, 69 %<br />
2. H 2, Pd(OH) 2/C<br />
EtOAc, 97 %<br />
3. Dess-Martin<br />
periodinane<br />
py, CH 2Cl 2, 91 %<br />
OMe<br />
Me<br />
Me<br />
N<br />
Me<br />
OMe<br />
t-BuLi<br />
+<br />
O O O OTBS Et2O, -78<br />
TMS TMS<br />
o I BnO<br />
C<br />
BnO<br />
H<br />
O<br />
OMe<br />
OMe<br />
Synthesis of the Southern H<strong>al</strong>f<br />
Me<br />
OMe H<br />
O<br />
OH<br />
AcO<br />
OMe H<br />
O<br />
OAc<br />
Me<br />
OTBS<br />
Me OTBS<br />
Me OTBS<br />
OMe<br />
OMe<br />
1. TBSOTf<br />
2,6-lutidine<br />
CH 2Cl 2, 98 %<br />
2. K 2OsO 2(OH) 4<br />
NMO, 90 days<br />
78 %, dr 6 : 1<br />
BnO<br />
OMe<br />
OMe<br />
O<br />
Me<br />
O<br />
Me<br />
O<br />
TMS TMS<br />
HO<br />
OMe H<br />
O<br />
OH<br />
Me<br />
OTBS<br />
OTBS<br />
Me OTBS<br />
OMe<br />
OMe<br />
Koert, U. <strong>et</strong>. <strong>al</strong>. Angew. <strong>Chem</strong>. Int. Ed. 2001, 40, 2063.