138-59-0Relevant articles and documents
Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid
Jiang, Shende,McCullough, Kevin J.,Mekki, Boualem,Singh, Gurdial,Wightman, Richard H.
, p. 1805 - 1814 (1997)
Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.
Shikimic acid and quinic acid: Replacing isolation from plant sources with recombinant microbial biocatalysis [4]
Draths,Knop, David R.,Frost
, p. 1603 - 1604 (1999)
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Stereochemistry of chorismic acid biosynthesis.
Hill,Newkome
, p. 5893 - 5894 (1969)
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An enantioconvergent route to (-)-shikimic acid via a palladium-mediated elimination reaction
Yoshida, Naoyuki,Ogasawara, Kunio
, p. 1461 - 1463 (2000)
(Matrix presented) (-)-Shikimic acid, the key intermediate in the shikimate pathway in plants and microorganisms, has been synthesized in an enantioconvergent manner from both enantiomeric starting materials by employing a palladium-mediated elimination reaction as the key step.
New phenolic compounds from Meehania urticifolia
Murata, Toshihiro,Miyase, Toshio,Yoshizaki, Fumihiko
, p. 385 - 390 (2011)
A new phenylethanoid glycoside, rashomoside A (1), a new phenolic glucoside, rashomoside B (2), and a new shikimic acid derivative (3) were isolated from Meehania urticifolia together with 12 known flavones (4-15), three known phenylethanoid glycosides (16-18), and 13 other compounds (19-31). The structure of each of these compounds was elucidated based on the results of spectroscopic analysis.
A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol
Ananthan, Bakthavachalam,Chang, Wan-Chun,Lin, Jhe-Sain,Li, Pin-Hui,Yan, Tu-Hsin
, p. 2898 - 2905 (2014/05/06)
Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.
A concise route to (-)-shikimic acid and (-)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis
Kancharla, Pavan K.,Doddi, Venkata Ramana,Kokatla, Hariprasad,Vankar, Yashwant D.
scheme or table, p. 6951 - 6954 (2010/02/28)
A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from d-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has bee
