Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
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HO<br />
HO<br />
O<br />
Me<br />
I<br />
OC<br />
Me<br />
H<br />
O<br />
O<br />
H<br />
H<br />
H<br />
CO 2Me<br />
OMEM<br />
OH<br />
1) TFAA, pyr<br />
2) Zn<br />
3) PrSLi<br />
27-GA3-coreytotal4.cdx 2/5/04 12:53 PM<br />
Gibberellic Acid Endgame: Corey<br />
1) ZnBr 2<br />
2) KOH, Na 2RuO 4<br />
HO<br />
OC<br />
Me<br />
95%<br />
1) mCPBA<br />
2) NaOH<br />
3) I 2, NaHCO 3<br />
O<br />
H<br />
H<br />
CO 2H<br />
OH<br />
HO 2C<br />
HO 2C<br />
GA 3<br />
H<br />
Me<br />
H<br />
Me<br />
H<br />
CO 2H<br />
H<br />
CO 2Me<br />
OH<br />
TsCl, NEt 3;<br />
MeOH<br />
OH<br />
Corey-Carney Acid<br />
Corey, JACS, 1978, 8034.
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