et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
et. al. J. Am. Chem. Soc.
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TES<br />
TBSOTf<br />
2,6-lutidine<br />
Synthesis of Vinylstannane M<strong>et</strong>hyl Ester (C 1 ~ C 11)<br />
O<br />
H<br />
(+) (Ipc) 2B<br />
BF 3 OEt 2<br />
CH 2Cl 2, 0 o C, 2 h, 97 % TES<br />
Me CO 2Et<br />
PPh 3<br />
toluene, 100 o C, 12 h<br />
E : Z > 9 : 1,<br />
90 % over two steps<br />
THF, -78 o C, 6 h<br />
TES<br />
TBSO<br />
TBSO<br />
Me<br />
Me<br />
Me Me<br />
CO 2Et<br />
NaBO 3 4H 2O<br />
THF / H 2O (2 / 1), rt, 12 h, 82 %<br />
1. O 3, CH 2Cl 2, -78 o C<br />
2. PPh 3, -78 o C then, rt, 12 h<br />
1. DIBAL-H<br />
toluene, -78 o C, 2 h, 90 %<br />
2. 0.05 eq. TPAP, NMO<br />
4 MS, CH 2Cl 2, rt, 30 min<br />
Å<br />
TES<br />
TES<br />
TES<br />
TBSO<br />
TBSO<br />
OH<br />
Me<br />
Me<br />
O<br />
H<br />
Me Me<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