et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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O<br />
OH<br />
Ac<strong>et</strong>ylenic Aldehyde – The Second Generation<br />
1. DDQ<br />
CH 2Cl 2 / H 2O (18 / 1)<br />
97 %<br />
2. SO 3 py, Et 3N<br />
DMSO / CH 2Cl 2 (2 / 1)<br />
96 %<br />
H 3C<br />
1. MeOTf<br />
2,6-di-t-butyl-4-m<strong>et</strong>hylpyridine<br />
CH 2Cl 2, 85 %<br />
2. AD-Mix-a<br />
dr 6 : 1, 85 %<br />
1. PMBCl, NaH, TBAI<br />
DMF, 71 %<br />
2.<br />
MgBr<br />
Et 2O, 90 %<br />
H<br />
CH 3<br />
OTBS<br />
OTBS<br />
OH<br />
O<br />
OMe<br />
H<br />
OH<br />
OPMB<br />
OH<br />
1. TBSOTf, 2,6-lutidine<br />
CH 2Cl 2, 97 %<br />
2. n-BuLi, MeI<br />
THF, 95 %<br />
(+) (Ipc) 2B<br />
Et 2O, -100 o C, 2 h<br />
then 30 % aq. H 2O 2<br />
3 M aq. NaOH, rt, 15 h<br />
dr 10 : 1, 95 %<br />
1. DMBA, CSA<br />
toluene, 110 o C, 99 %<br />
2. DIBAL-H<br />
CH 2Cl 2, 70 %<br />
3. SO 3 py, Et 3N<br />
DMSO / CH 2Cl 2 (2 / 1)<br />
90 %<br />
H 3C<br />
CH 3<br />
CH 3<br />
OTBS<br />
OH<br />
OTBS<br />
OTBS<br />
OMe<br />
OPMB<br />
ODMB<br />
Nicolaou, K. C. <strong>et</strong>. <strong>al</strong>. J. <strong>Am</strong>. <strong>Chem</strong>. <strong>Soc</strong>. ASAP<br />
O<br />
H
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