R.; Lober, S.; Hubner, H.; Gmeiner, P., Click chemistry on solid phase: parallel synthesis of -benzyltriazole carboxamides as super-potent G-protein coupled receptor ligands.
We will illustrate this approach with examples, starting with synthesis of benzene derivatives. Starting point is usually fairly obvious – simple benzene derivatives or perhaps benzene itself.
Benzene-free synthesis of hydroquinone — MSU Scholars
N2 - All current routes for the synthesis of hydroquinone utilize benzene as the starting material. An alternate route to hydroquinone has now been elaborated from glucose. While benzene is a volatile carcinogen derived from nonrenewable fossil fuel feedstocks, glucose is nonvolatile, nontoxic, and derived from renewable plant polysacharrides. Glucose is first converted into quinic acid using microbial catalysis. Quinic acid is then chemically converted into hydroquinone. Under fermentor-controlled conditions, Escherichia coli QP1.1/pKD12.138 synthesizes 49 g/L of quinic acid from glucose in 20% (mol/mol) yield. Oxidative decarboxylation of quinic acid in clarified, decolorized, ammonium ion-free fermentation broth with NaOCl and subsequent dehydration of the intermediate 3(R),5(R)-trihydroxycyclohexanone afforded purified hydroquinone in 87% yield. Halide-free, oxidative decarboxylation of quinic acid in fermentation broth with stoichiometric quantities of (NH4)2Ce(SO4)3 and V2O5 afforded hydroquinone in 91% and 85% yield, respectively. Conditions suitable for oxidative decarboxylation of quinic acid with catalytic amounts of metal oxidant were also identified. Ag3PO4 at 2 mol % relative to quinic acid in fermentation broth catalyzed the formation of hydroquinone in 74% yield with K2S2O8 serving as the cooxidant. Beyond establishing a fundamentally new route to an important chemical building block, oxidation of microbe-synthesized quinic acid provides an example of how the toxicity of aromatics toward microbes can be circumvented by interfacing chemical catalysis with biocatalysis.
certainly practical if benzene where the starting material
10 Show how the molecule below can be synthesized startingwith isopropanol, ethene, and any other reagents. Show the Zwitter ion for thisamino acid.
Starting with benzene, provide a synthesis for the following compound
7 Show how the molecule below can be synthesized startingwith straight chain hydrocarbons of 6 carbons or less, a total of fourfunctional groups on the starting materials and any other reagents.
Benzene - National Cancer Institute
Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the 3,4-atisane diterpenoid (−)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels–Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of -3,4-abietane diterpenoids using an intramolecular oxidative dearomatization.
How can the answer be improved?
3 Show how the molecule below can be synthesizedstarting with 1,3-pentadiene and benzene using a pathway that lead to theformation of an epoxide.