Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
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MeO<br />
TBSO<br />
6 steps<br />
52%<br />
TBSO<br />
CO 2Me<br />
OC<br />
O<br />
H<br />
OH<br />
H<br />
OH<br />
I<br />
O 2N<br />
O O<br />
O<br />
CO 2Me<br />
N-tBu<br />
= L<br />
NiBr<br />
2 2<br />
41-anteridiogens3-Corey.cdx 2/5/04 3:31 PM<br />
Total Syn<strong>the</strong>sis <strong>of</strong> An<strong>the</strong>ridic Acid: Corey<br />
H<br />
TBSO<br />
TBSO<br />
H<br />
EtAlCl2 51% overall<br />
O O<br />
53%<br />
O O<br />
80%<br />
O 2N<br />
7 steps<br />
76%<br />
TBSO<br />
H<br />
1) TMSCl, LDA<br />
TBSO<br />
2) Eschemoser's<br />
salt, MeI, iPr2NEt 60%<br />
OC<br />
OH<br />
H<br />
N 2<br />
O O<br />
O<br />
H<br />
O<br />
1) Cu(II)L 2<br />
2) Br 2; DBU<br />
CO 2Me<br />
1) MeCO 3H<br />
2) LiNEt 2<br />
H<br />
57%<br />
4 steps<br />
90%<br />
TBSO<br />
HO<br />
OC<br />
O<br />
H<br />
H<br />
H<br />
O O<br />
OH<br />
CO 2H<br />
an<strong>the</strong>ridic acid<br />
original structure proposed as 3β−OH<br />
Corey, Myers, JACS, 1985, 5574.<br />
H
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