et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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HO<br />
O<br />
Me<br />
O<br />
1. DIBAL-H<br />
2. MnO 2<br />
3. Me CO2Et PPh 3<br />
86 % three steps<br />
1. DIBAL-H, 80 %<br />
2. MnO 2<br />
3. Me CO2Et PPh 3<br />
60 % two steps<br />
1. TBSOTf<br />
2,6-lutidine<br />
CH 2Cl 2, 90 %<br />
2. DIBAL-H<br />
CH 2Cl 2, 95 %<br />
TBSO<br />
TESO<br />
TBSO<br />
Synthesis of the Northern H<strong>al</strong>f<br />
I<br />
Me<br />
Me<br />
TBSO<br />
Me<br />
Me<br />
Me<br />
Me<br />
O<br />
CO 2Et<br />
Me<br />
Me CO 2Et<br />
OH<br />
1.<br />
Me CO 2Et<br />
PPh 3<br />
2. TESCl<br />
imidazole<br />
82 % two steps<br />
1. camphorsulfonic acid<br />
MeOH, CH 2Cl 2, 95 %<br />
2. Dess-Martin periodinane<br />
3. CrCl 2, CHI 3, hydroquinone<br />
69 % two steps<br />
TBSO<br />
TESO<br />
TBSO<br />
I<br />
Me<br />
Me<br />
Me<br />
CO 2Et<br />
Me<br />
Me<br />
CO 2Et<br />
Koert, U. <strong>et</strong>. <strong>al</strong>. Angew. <strong>Chem</strong>. Int. Ed. 2001, 40, 2063.
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