Structure and stereochemistry of galbanic acid

Synthesis, biosynthesis and biological activities of galbanic acid – A review

“…They synthesized GA and determined absolute configuration at C10 by X-ray crystallographic analyses of the precursors. They confirmed the structure and the stereochemistry of GA (1c) reported by Bagirov et al (1980) (Corbu et al, 2008).…”

“…Kunz et al (1937) were the first group to report GA from galbanum resin. In 1955, Pigulevskii et al ascribed the structure 1a for GA (Bagirov et al, 1980;Pigulevskii & Naugol'naya, 1955) (Figure 2). In 1973, Borisov et al (1975) revised the structure of GA as 1b on the basis of 1 H-NMR and mass spectra.…”

“…In 1973, Borisov et al (1975) revised the structure of GA as 1b on the basis of 1 H-NMR and mass spectra. Later, Bagirov et al (1980) proposed a different structure (1c) for GA, as shown in Figure 2. In the proposed structure by Bagirov et al (1980), the position of double bond and arrangements of methyl groups in the sesquiterpene part of GA structure differed from the previous ones.…”

“…Later, Bagirov et al (1980) proposed a different structure (1c) for GA, as shown in Figure 2. In the proposed structure by Bagirov et al (1980), the position of double bond and arrangements of methyl groups in the sesquiterpene part of GA structure differed from the previous ones. After that, Lee et al (1998) proposed a different stereochemistry for GA on the basis of 2D NMR techniques (1d).…”

“…The problem was that GA does not have a crystalline form, which provides a condition for an X-ray crystallographic analysis. However, researchers resolved this problem by X-ray crystallographic analysis of GA precursors (Bagirov et al, 1980;Borisov et al, 1975;Corbu et al, 2008;Lee et al, 1998).…”