et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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TBSO<br />
OTBS<br />
Synthesis of Fully Protected Apoptolidin<br />
O<br />
Me<br />
Me<br />
MeO<br />
O<br />
Me<br />
Me<br />
Me<br />
TBSO<br />
Me<br />
HO<br />
A<br />
OH<br />
A<br />
O<br />
MeO<br />
Cl2AcO Me<br />
Me<br />
Me<br />
MeO<br />
O<br />
Me<br />
Me<br />
Me OH Me<br />
MeO<br />
HO<br />
Me<br />
O<br />
O<br />
OMe H<br />
O<br />
OTBS<br />
O<br />
O<br />
OH H<br />
O<br />
OH<br />
Me O<br />
OMe<br />
TESO Me<br />
Me O<br />
O Me<br />
O<br />
OMe<br />
O<br />
O Me<br />
O<br />
HO Me<br />
O<br />
Me<br />
D E<br />
Me<br />
D E<br />
OTBS<br />
OMe<br />
OH<br />
OMe<br />
1. HF py<br />
THF, 96 h<br />
2. Et 3N<br />
MeOH, rt, 3.5 h<br />
40 % over two steps<br />
3. TsOH<br />
THF / H 2O (1 / 1)<br />
0 o C, 2.5 h, 60 %<br />
36 steps (the longest linear)<br />
0.28 % yield<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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