12 -Hydroxyeicosatetraenoic acid methyl

Dehydroabietyl isocyanate, [39], was used by Falck et al. to determine the absolute configuration of hydroxyeicosatetraenoic acid methyl esters in a study of the enzymatic epoxidahon of arachidonic acid (175). In another study of similar metabolites, the stereochemical identity of 12-hydroxy-5,8,10,14-eicosatetraenoic acid derived from the lesional scale of patients with psoriasis was studied via separation of the enantiomers after derivatization with [39] (176). In these studies (175,176), LC separation of the derivatives was used. CDA [39] can be prepared from commercially available resolved dehydroabietylamine. It would be worthwhile to examine the applicability of this CDA to the resolution of other compounds. 

These GC conditions are suitable for analyzing many prostaglandins, thromboxanes, leuko-trienes, and other metabolites of arachidonic acid, such as the hydroxyeicosatetraenoic (HETE) acids. However, the 5-, 12-, and 15-HETE isomers are difficult to separate using GC methods. Sometimes the methyl ester-TMS derivatives provide a better GC separation, or for ketoprostaglandins, the MO-methyl ester-TMS derivatives often give a better separation... 

Earlier work on the s mthesis of chiral a-hydroxyaldehydes (see Vol. 21, p. 174 and Vol. 20, p.270) from d-mannitol-derived diepoxides has been extended to the synthesis of methyl (i )- and (S)-9-hydroxyeicosatetraenoates (methyl 9R-and 9S-HETE), and to coriolic acid [13(S)-hydroxy-9Z,llE-octadecadienoic acid] and its 13(S)-N-tosylamino-analogue. made from a bis-aziridine (Vol. 20, p.271). 8... 

---