Total synthesis of Vidolicine

Vidolicīna totālā sintēze. Kazak M., zinātniskie vadītāji: Dr. chem. prof. E. Sūna E; Dr. chem. K. Shubin. Maģistra darbs, 53 lappuses, 43 attēli, 1 tabula, 55 literatūras avoti. Latviešu valodā. Maģistra darbs ir veltīts Aspidosperma alkaloīdu grupas pārstāvja vidolicīna stereoselektīvajai totālajai sintēzei. Totālās sintēzes atslēgas stadijas ir augsti diastereoselektīva N-terc-butilsulfinilimīna aldola-tipa reakcija un allijodīda secīga fotoķīmiska izomerizācija-ciklizācija. Svarīgāko starpsavienojumu struktūra un stereocentru absolūtā konfigurācija ir pierādīta ar KMR spetroskopijas un rentgenstaru difrakcijas metodēm.Total synthesis of Vidolicine. Kazak. M., supervisors: Dr. chem. prof. E. Sūna; Dr. chem. K. Shubin. Master’s thesis, 53 pages, 43 figures, 1 table, 55 literature references. In Latvian. Master’s thesis is focused on stereoselective total synthesis of vidolicine, a representative alkaloid of Aspidosperma family. Key steps of the synthesis are highly diastereoselective aldol-type reaction of tert-butylsulfinylimines and one pot sequential photochemical isomerization-cyclization of allyl iodide. Structure of the most important intermediates and absolute configuration of stereogenic centers was proved by NMR methods and X-ray crystallographic analysis

Enantioselective aldol and Mannich type reactions of metallated tert-butylsulfinylimines

Metalētu terc-butilsulfinilimīnu enantioselektīvās aldola tipa un Manniha tipa reakcijas. Kazak M., zinātniskie vadītāji: Dr. chem. Šubin K; asoc. prof., Dr. chem. Sūna E. Bakalaura darbs, 44 lappuses, 32 attēli, 7 tabulas, 24 literatūras avoti. Latviešu valodā. Darbā veikta vairāku N-terc-butilsulfinilimīnu sintēze un izpētīta metalētu N-terc-butilsulfinilimīnu Manniha tipa reakcijas un aldola tipa reakcijas. Literatūras apskatā aplūkota informācija par N-terc-butilsulfinilimīnu iegūšanu un stereoselektīvajām reakcijām. terc-BUTILSULFINILIMĪNI, MANNIHA REAKCIJA, ALDOLĀ REAKCIJA.Enantioselective aldol-type and Mannich-type reactions of metalated tert-butanesulfinylimines. Kazak. M., supervisors: Dr. chem. Shubin K; asoc. prof., Dr. chem. Sūna E. Bachelor’s thesis, 44 pages, 32 figures, 7 tables, 24 literature references. In Latvian. Thesis is dedicated to synthesis of N-tert-butanesulfinylimines and investigation of their aldol-type and Mannich-type reactions. Review of literature covers information about synthesis of N-tert-butanesulfinylimines and their stereoselective reactions. tert-BUTANESULFYNILIMINES, MANNICH REACTION, ALDOL REACTION

Diastereoselective Hydroxymethylation of Cyclic N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source

A stable and easy-to-handle source of anhydrous monomeric formaldehyde is used

Stereodivergent Synthesis of Pseudotabersonine Alkaloids

International audienc

Diastereoselective Hydroxymethylation of Cyclic <i>N</i>-<i>tert</i>-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source

Hydroxymethylation of cyclic <i>tert</i>-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to <i>syn</i>- or <i>anti</i>-1,3-amino alcohols

Diastereoselective Hydroxymethylation of Cyclic <i>N</i>-<i>tert</i>-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source

Hydroxymethylation of cyclic <i>tert</i>-butanesulfinylketimine-derived lithium enamides with methoxymethanol proceeds with excellent diastereoselectivity (99:1 dr). Methoxymethanol is a stable and easy-to-handle source of anhydrous monomeric formaldehyde in the reaction with lithium enamides. Cyclic α-hydroxymethyl ketimines undergo highly diastereoselective reduction to <i>syn</i>- or <i>anti</i>-1,3-amino alcohols