1 Introduction
1.1 Hederagonic Acid
Hederagonic acid (23-hydroxy-3-oxo-olean-12-en-28-oic acid) (1) is a naturally occurring pentacyclic triterpenoid based on the oleanane scaffold
(Figure 1.1). The molecule is related to hederagenin (2), found in Hedera
helix (common ivy).
[6] Hederagonic acid (1) can in principle be accessed
from hederagenin (2) via oxidation of the C-3 hydroxy group. The first
synthesis of 23-O -methyl hederagonic acid methyl ester was reported by
Jacobs in 1925.
[7] 23-O -Methyl hederagonic acid methyl ester was obtained
via oxidation of 23-O -methyl hederagenin with potassium permanganate.
[7]
O
H
H
OH
O
H
HO
A
D
E
H
H
H
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
28
24
23
25
26
29
27
30
A
E
HO
H
H
OH
O
H
HO
A
D
E
H
Hederagonic acid (1)
C30H46O4
470.69 g mol −1
Hederagenin (2)
C30H48O4
472.71 g mol −1
Oleanane scaffold
C30H52
412.75 g mol −1
Figure 1.1: Structure of hederagonic acid (1), hederagenin (2) and the
oleanae scaffold with applied atom numbering.
The first reported isolation of hederagonic acid was by Agarwal and
Rastogi from Viburnum erubescens Wall in 1974.
[8] It should be mentioned
here, that the use of the therein proposed name ‘hederagenic acid’ was
© The Editor(s) (if applicable) and The Author(s), under exclusive license to
Springer Fachmedien Wiesbaden GmbH, part of Springer Nature 2020
C. Knittl-Frank, A Concise Semisynthesis of Hederagonic Acid, BestMasters,
https://doi.org/10.1007/978-3-658-30011-1_1