Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
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SEMO<br />
MOMOH 2C<br />
91%<br />
HO 2C<br />
OC<br />
H<br />
H<br />
Me<br />
H<br />
Me<br />
O<br />
H<br />
Me<br />
H<br />
CH 2OMOM<br />
8 steps<br />
H<br />
CO 2H<br />
H<br />
CO 2H<br />
34-GA3-yamadatotal2.cdx 2/5/04 2:50 PM<br />
Yamada: Syn<strong>the</strong>sis <strong>of</strong> Gibberellic Acid<br />
1) I 2, NaHCO 3<br />
2) DBU<br />
OMOM<br />
OMOM<br />
OMOM<br />
1) MOMCl, iPr 2NEt<br />
2) LDA<br />
99%<br />
HO<br />
HO 2C<br />
OC<br />
O<br />
H<br />
Me<br />
H<br />
Me<br />
H<br />
CO 2H<br />
H<br />
CO 2MOM<br />
OH<br />
GA 3<br />
6 steps (Corey et al)<br />
MOM-protected<br />
Corey-Carney Acid<br />
OMOM<br />
30% <strong>from</strong> tri-MOM-e<strong>the</strong>r<br />
Yamada, TL, 1989, 971.
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