Chemical synthesis of shikimic acid and its analogues

Tetrahedron

Volumn 54, Issue 19, 1998, Pages 4697-4753

  Jiang, Shende ^a   Singh, Gurdial ^a  

^a UNIVERSITY OF SUNDERLAND   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CARBOHYDRATE; QUINIC ACID; SHIKIMIC ACID; SHIKIMIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0032079254     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00016-7     Document Type: Review

References (260)

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2. 2. This author, J. F. Eykman, is sometimes referred in the literature as J. F. Eijkman. However, in most reviews and books on this subject his name had unfortunately been misspelled as J. F. Eykmann.
3. 3. Illicium religiosum Sieb. et Zucc., synonym Illicium anisatum L., is an evergreen tree which is native to China and was introduced into Japan at an early date by Buddhist priests. It is called Mang ts'ao (or Mang cao) in Chinese, Shikimi-no-ki in Japanese, and commonly known as Japanese star anise. In China this poisonous plant has been used locally as a medicine and also used to kill fish. In Japan it is often planted in cemeteries and Buddhist temple grounds as an offering flower and used in religious ceremonies, whence the name Illicium religiosum. Sometime, the name Illicium anisatum L. was used improperly to refer to the Chinese star anise which should be termed as Illicium verum Hook. The Chinese star anise (Illicium verum Hook.) and the Japanese star anise (Illicium religiosum Sieb. et Zucc., Illicium anisatum L.) are different, although their fruits are barely distinguishable. In Asia the fruit of the former is used as a spice, and in the West it is used to aromatise cordials and liqueurs. In the last century, mistaken identity and intentional mixing of the two fruits as an adulterated spice often resulted in many cases of poisoning, which was also the reason behind Eykman's investigation into the chemical constituents of Illicium religiosum Sieb. et Zucc. (see: Eykman, J. F. Pharm. J. Trans., 1881, 11, 1046). Eykman isolated (-)-shikimic acid 1 from the fruit of Illicium religiosum Sieb. et Zucc. in 1885 (see: ref. 1), and in the following year he also obtained (-)-shikimic acid 1 from the fruit of Illicium verum Hook. which he at that time termed as Illicium anisatum in his article (see: Eykman, J. F. Recl. Trav. Chim. Pays-Bas, 1886, 5, 299).
4. 3. Illicium religiosum Sieb. et Zucc., synonym Illicium anisatum L., is an evergreen tree which is native to China and was introduced into Japan at an early date by Buddhist priests. It is called Mang ts'ao (or Mang cao) in Chinese, Shikimi-no-ki in Japanese, and commonly known as Japanese star anise. In China this poisonous plant has been used locally as a medicine and also used to kill fish. In Japan it is often planted in cemeteries and Buddhist temple grounds as an offering flower and used in religious ceremonies, whence the name Illicium religiosum. Sometime, the name Illicium anisatum L. was used improperly to refer to the Chinese star anise which should be termed as Illicium verum Hook. The Chinese star anise (Illicium verum Hook.) and the Japanese star anise (Illicium religiosum Sieb. et Zucc., Illicium anisatum L.) are different, although their fruits are barely distinguishable. In Asia the fruit of the former is used as a spice, and in the West it is used to aromatise cordials and liqueurs. In the last century, mistaken identity and intentional mixing of the two fruits as an adulterated spice often resulted in many cases of poisoning, which was also the reason behind Eykman's investigation into the chemical constituents of Illicium religiosum Sieb. et Zucc. (see: Eykman, J. F. Pharm. J. Trans., 1881, 11, 1046). Eykman isolated (-)-shikimic acid 1 from the fruit of Illicium religiosum Sieb. et Zucc. in 1885 (see: ref. 1), and in the following year he also obtained (-)-shikimic acid 1 from the fruit of Illicium verum Hook. which he at that time termed as Illicium anisatum in his article (see: Eykman, J. F. Recl. Trav. Chim. Pays-Bas, 1886, 5, 299).
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