et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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Cl<br />
Synthesis of Fully Protected Apoptolidin<br />
O<br />
Cl Cl<br />
Cl<br />
THF, 0 o C then rt, 5 h<br />
1. (Cl 2Ac) 2O, py<br />
0 o C, 5 min, 90 %<br />
2. PPTS<br />
0 oC, 15 h, 80 %<br />
, Et 3N DMAP<br />
toluene, rt, 12h<br />
27 % over 3 steps<br />
TBSO<br />
OTBS<br />
A<br />
O<br />
TBSO<br />
OTBS<br />
O<br />
Me<br />
Me<br />
MeO<br />
O<br />
Me<br />
Me<br />
Me<br />
TBSO Me<br />
Me<br />
Me<br />
A<br />
MeO<br />
O<br />
Me<br />
Me<br />
Me<br />
TBSO<br />
Me<br />
MeO<br />
Cl2AcO Me<br />
O<br />
O<br />
OMe H<br />
O<br />
OTBS<br />
MeO<br />
HO<br />
Me OH<br />
Me<br />
OMe<br />
O<br />
O<br />
OMe H<br />
O<br />
OTBS<br />
Me OTES<br />
OMe<br />
Nicolaou, K. C. <strong>et</strong>. <strong>al</strong>. J. <strong>Am</strong>. <strong>Chem</strong>. <strong>Soc</strong>. ASAP
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