Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
Highlights from the Synthesis of Gibberellins:
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MeO<br />
PhOCO<br />
MeO<br />
Mander: A-Ring Assembly through Birch Reduction/Alkylation<br />
CO 2Me<br />
OC<br />
Br<br />
Me<br />
CO 2H<br />
O<br />
H<br />
CO 2H<br />
H<br />
CO 2Et<br />
H<br />
CO 2Me<br />
31-GA3-mandertotal2.cdx 2/5/04 1:03 PM<br />
OMOM<br />
O<br />
O<br />
O<br />
O<br />
OMOM<br />
O<br />
O<br />
1) KOtBu, K, NH 3; MeI<br />
2) CH 3CHN 2<br />
66%<br />
KHCO 3, KBr 3<br />
86%<br />
Na, NH 3; MeI<br />
C7 ester controls alkylation<br />
MeO<br />
MeO<br />
MeO 2C<br />
MeO 2C<br />
PhOCO<br />
HO 2C<br />
Me<br />
Me<br />
H<br />
Me<br />
CO 2Me<br />
H<br />
CO 2Et<br />
H<br />
CO 2Et<br />
O<br />
O<br />
OMOM<br />
O<br />
O<br />
OMOM<br />
O<br />
O<br />
4 steps<br />
Mander, JACS. 1980, 6626.<br />
Baker, Chem. Com. 1972, 951.
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