Prostaglandin Nomenclature - The Stoltz Group
Prostaglandin Nomenclature - The Stoltz Group
Prostaglandin Nomenclature - The Stoltz Group
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I<br />
PMBO<br />
OTBS<br />
(10 equiv)<br />
-40 °C, 42h<br />
(38% yield)<br />
O<br />
TBSO<br />
Vinyl Cyclopropane Rearrangement Route - Wulff, 1990<br />
C 5H 11<br />
C 5H 11<br />
OPMB<br />
t-BuLi (2 equiv)<br />
Et 2O, -78 → 0 °C, 2h<br />
then Cr(CO) 6 (1.4 equiv)<br />
then TBAF<br />
TBSO<br />
CO 2Me<br />
OAc<br />
PMBO<br />
C 5H 11<br />
(OC) 5Cr<br />
DDQ (1.5 equiv)<br />
PMBO<br />
Murray, C. K.; Yang, D. C.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 5660–5662.<br />
O -<br />
filtered<br />
NBu 4 +<br />
Bu 2O, 190 °C, 2h<br />
(85% yield)<br />
CH 2Cl 2/H 2O, 10 °C, 1h, 80% yield<br />
HF/pyr, MeCN, 0 → 25 °C, 15 h<br />
86% yield<br />
C 5H 11<br />
AcO<br />
TBSO<br />
O<br />
HO<br />
AcBr (1 equiv)<br />
DCM, -40 °C, 1 h<br />
OH<br />
C 5H 11<br />
OPMB<br />
C 5H 11<br />
(OC) 5Cr<br />
then<br />
I<br />
CO 2Me<br />
PGE 2 Methyl ester & C15 epimer<br />
OAc<br />
PMBO<br />
n-BuLi (2 equiv)<br />
HMPA<br />
Ph 3SnCl<br />
First natural product synthesis employing a Fischer Carbene as a key intermediate<br />
C 5H 11<br />
CO 2Me
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