Organic Reactions & Synthesis

CHEM 6352 Organic Reactions & Synthesis Chiral Pool Amino Acids: NH SMe H H 2N CO2H H 2N alanine CO2H H 2N valine CO2H H 2N leucine CO2H H 2N isoleucine CO2H H 2N methionine CO2H HO N CO2H H proline H 2N CO2H H 2N serine CO2H H 2N threonine CO2H H 2N glutamine CO2H NH 2 CO2H H N NH 2 H 2N asparagine CO2H H 2N lysine NH 2 NH CO2H arginine CO2H histidine NH 2 H 2N CO2H aspartic acid H 2N CO2H L-homocystine (D also available, both expensive) H 2N NH 2 H 2N CO2H OH OH CO2H I 5-hydroxylysine (collagen) ornithine I I O O HO H N N CO2H H 4-hydroxyproline (collagen) H 2N CO2H L-phenylglycine (D also available) H 2N CO2H citrulline O I OH NH 2 H 2N CO2H L-2-aminoadipic acid (expensive) H 2N cysteine OH OH Uncommon Amino Acids: SH CO2H O N H H 2N H 2N tyrosine N O H 2N SH NH 2 H CO2H tryptophan OH O OH H 2N phenylalanine CO2H L-thyroxine (expensive) H 2N O CO2H glutamic acid Hydroxy Acids O O OH OH L-lactic acid O HO OH OH O HO OH OH OH O OH O OH (+)-mandelic acid L-malic acid (S,S)-(–)-tartaric acid ((–)-isomer also available) (D-isomer also available) (R,R-isomer also available) Others available through diazonium chemistry of amino acids Pharmaceuticals: SH NH 2 O CO2H NH 2 CO2H H 2N D-penicillamine (+)-amphetamine (L-isomer also available) pregabalin O O H 2N P HO OH phosphomycin NH O D-cycloserine Aminoalcohols: OH OH HO HO HN HN HN (–)-ephedrine (+)-pseudoephedrine ((+)-isomer also available) ((–)-isomer also available) OH OH HO OH OH (–)-phenylephrine NH 2 HN HO (–)-epinephrine NH 2 HO OH NH OH NH 2 HO (–)-trans-1-amino-2-indanol (–)-metaraminol (–)-norephedrine ((+)-isomer also available) ((+)-isomer also available) Others available through reduction of amino acids (–)-cis-1-amino-2-indanol ((+)-isomer also available) Carbohydrates: Aminoalcohols Aldoses: Expensive: O HO OH O HO H OH D-glyceraldehyde OH HO O HO H OH HO H OH D-erythrose O OH OH O OH HO HO O D-ribose O HO HO OH OH O OH HO OH D-arabinose (L also available) O HO OH HO OH D-mannose OH OH O HO OH D-xylose (L also available) OH OH HO O OH HO OH OH D-glucose OH HO OH D-galactose OH OH D-lyxose O HO OH OH OH D-allose D-threose OH OH HO Less expensive: HO O NHAc OH N-Acetyl-D-glucosamine Ketoses: Expensive: OH HO O OH HO OH OH D-tagatose Less expensive: OH O OH HO OH HO O L-erythrulose OH OH O OH HO OH D-fructose OH O OH HO OH L-sorbose OH OH OH D-lyxose Carbohydrate Derivatives: O OH OH HO D-mannose OH OH O OH OH mannitol HO OH OH erythritol HO D-threose OH OH threitol D-glyceraldehyde acetal OH D-erythrose H O HO Starch (glucose) O O Terpenes: more expensive H O camphor (+)-!-pinene ((–)-isomer also available) (–)-"-pinene O OH O H (+)-2-carene H O (–)-menthol (–)-menthone (+)-pulegone (–)-perillaldehyde ((+)-isomer also available) ((–)-isomer is available, but is expensive) O (–)-!-phellandrene (+)-"-citronellene OH OH (–)-limonene (–)-carvone ((+)-isomer also available) ((+)-isomer also available) (–)-"-citronellol ((+)-isomer also available) H O H O O OH H O (–)-!-santonin O nepetalactone (catnip) (–)-terpinen-4-ol Readily Available Artificially-Derived: O NH 2 O (+)-terpineol Cl O (+)-epichlorhydrin ((–)-isomer also available) NH 2 NH 2 (–)-1,2-diaminocyclohexane ((+)-isomer also available, but more expensive) (–)-!-Me-benzylamine ((+)-isomer also available) Wieland-Miescher ketone both enantiomers available O NH 2 NH 2 O Hajos-Parrish ketone (+)-1,2-Diphenylethylenediamine both enantiomers available ((–)-isomer also available, both are expensive)