Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
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H<br />
H<br />
O<br />
H<br />
O<br />
O<br />
O<br />
O<br />
O<br />
O<br />
NaOMe<br />
H<br />
O<br />
H<br />
H<br />
O<br />
O<br />
O<br />
OH<br />
Me<br />
OH<br />
OH<br />
tBuMgCl<br />
H<br />
OH<br />
SMe<br />
14 steps<br />
MeO2C O SMe<br />
O<br />
MeO2C O O<br />
CO2Me House, JOC, 1973, 1398.<br />
O<br />
Zn,<br />
HOAc<br />
H<br />
OH<br />
H Br<br />
CO2Me Ziegler, JOC, 1971, 3707. (model system)<br />
MeO 2C<br />
CO 2Me<br />
45-cd-ring stragedy.cdx 2/5/04 3:43 PM<br />
Aldol C/D Ring Strategies Not Discussed<br />
Hg(II)O<br />
H 2SO 4<br />
HCl,<br />
acetone<br />
MeO 2C<br />
Ireland, JOC, 1966, 2530. (toward kaurenes)<br />
Takano, Ogasawara, Chem. Com., 1981, 635.<br />
Takano, Ogasawara, Chem. Com., 1981, 637.<br />
H<br />
OH
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