Gibberellic acid

Type of derived tetracyclic terpenoids

Gibberellin A3

Dr. Dilip (M.Sc;B.Ed; Ph.D) 1

1. M.F= C19H22O6
2. Presence of two D.B

3. Presence of two-OH group

Diacetate Reduction product of g.a gives ketone so 20

One -OH is tertiary and other is secondary

Dr. Dilip (M.Sc;B.Ed; Ph.D) 2

4. Presence of one–COOH group
NaHCO3 , Monomethyl ester

4-O is used up now what is

about remaining two O?????
5. Presence of lactone ring

Two equivalents of alkali for neutralization

Dr. Dilip (M.Sc;B.Ed; Ph.D) 3

5. Presence of 4 rings

DBE=C+1-H/2

Dr. Dilip (M.Sc;B.Ed; Ph.D) 4

6. Hydrolysis of gebberellic acid
Carbon skeleton is IV in I-III

II contained
CO
(Oxime)
And –COOH
group =Ester
III is
contained OH
(Acetyl)
And –COOH
group Ester
Fluorene
Dr. Dilip (M.Sc;B.Ed; Ph.D) 5
7. Presence of hexahydrofluorene nucleus in gebberic acid (II)
II contained
CO
(Oxime)
No enolisable H And –COOH

group =Ester
SeO2 Oxidizing
agent,1.allylic=OH
2. A ketone=a
Position of COOH
diketone

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8. Position of CH2CO bridge group

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9. Degradation of allogibberic acid(III) and exocyclic methylene group

Dr. Dilip (M.Sc;B.Ed; Ph.D) 9

10. Position of CO group

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11. Isomers

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12. Position of D.B and Position of lactone ring

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Dr. Dilip (M.Sc;B.Ed; Ph.D) 14
 Thanks
Wait
Self Study
Biosynthetic studies on triterpenoids
and tetraterpenoids

Dr. Dilip (M.Sc;B.Ed; Ph.D) 15