A STEREOSPECIFIC SYNTHESIS OF dl-SHIKIMIC ACID¹

Abstract

COMMUNICATIOKS TO THE EDITOR 2909 acid3 and the oxidized protein was partially hydrolyzed (12 N HC1, 105', 3 hours). The hydroly-(1) C 0 Overberger, R J Ehrig and D 'Tanner, Tms J O U K~ 11 76,

Shikimic acid as intermediary model for the production of drugs effective against influenza virus

“…The most common method for synthesis of racemic SA was obtained by Diels Alder reaction with (1E, 3E)-1,4-diacetoxy-1,3-butadiene, and in this method acrylic acid was used as starting material for the SA synthesis with 15% yield [27,28]. Pinus sylvestris Summer, winter needles Bochkov et al [26] Other studies have also reported that SA was synthesized from (À)-quinic acid obtained from cinchona bark [29].…”

The biosynthesis of phenazines: incorporation of [2H]shikimic acid

“…The material from (16) was contaminated with (22), and also (24) which presumably arises from (26) as an impurity in the bromo-compound (16). Hydrogen fluoride catalysed isomerization of (20) gave, after deacetylation, Comparison of the n.m.r.…”

Asymmetric syntheses of (−)-methyl shikimate and (−)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization

“…To a solution of 9 (0.260 g, 0.69 mmol) in dichloromethane (10 mL), was added 1,8-diazabicyclo [5,4,0.530 g,3.48 mmol). The reaction mixture was then stirred at room temperature for 6 h. After the reaction was complete, dichloromethane (20 mL) and dilute aqueous HCl solution (2 N, 25 mL) were added, and stirring was continued for 15 min.…”

“…4 A series of methods over the last decades have been found to synthesize racemic or enantiomerically pure shikimic acid, and an excellent review has summarized these methods. 5 They can be briefly classified into four categories: (a) syntheses based on the Diels-Alder reaction; 3,4,6 (b) syntheses from benzene and its derivatives; 7 (c) syntheses from (À)-quinic acid; 8 and (d) syntheses from carbohydrates. 9 Carbohydrates that are naturally abundant and inherently rich in chiral centers have played an important role in the syntheses of natural products.…”