et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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TBSO<br />
Me<br />
HF, py<br />
Me<br />
THF, 55 %<br />
OH<br />
Me<br />
Me<br />
Me CO 2Et<br />
OMe<br />
AcO<br />
Me<br />
Me<br />
HO<br />
OAc<br />
OMe H<br />
O<br />
Compl<strong>et</strong>ion of the Synthesis<br />
OTBS<br />
Me<br />
Me OTBS<br />
OH<br />
Me<br />
Me<br />
Me<br />
OMe<br />
HO<br />
Me<br />
OMe<br />
O<br />
O<br />
OMe H<br />
O<br />
OH<br />
1. LiOH, 87 %<br />
2. Cl<br />
O<br />
Cl Cl<br />
Cl<br />
Et 3N, DMAP, 74 %<br />
Me OH<br />
OMe<br />
TBSO<br />
Me<br />
Me<br />
Me<br />
Me<br />
OH Me<br />
OMe<br />
HO<br />
Me<br />
O<br />
O<br />
OMe H<br />
O<br />
OTBS<br />
Me OTBS<br />
19 steps (the longest linear)<br />
2.8 % yield<br />
OMe<br />
Koert, U. <strong>et</strong>. <strong>al</strong>. Angew. <strong>Chem</strong>. Int. Ed. 2001, 40, 2063.