Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

An efficient and highly stereoselective fluorinative aza-semipinacol rearrangement is described. The catalytic reaction requires use of Selectfluor in combination with the chiral, enantiopure phosphate anion derived from acid <b>L3</b>. Under optimized conditions, cyclopropylamines <b>A</b> were transformed into β-fluoro cyclobutylimines <b>B</b> in good yields and high levels of diastereo- and enantiocontrol. Furthermore, the optically active cyclobutylimines were reduced diastereoselectively with L-Selectride in the corresponding fluorinated amines <b>C</b>, compounds of significant interest in the pharmacological industry

Targeted Isolation of Monoterpene Indole Alkaloids from <i>Palicourea sessilis</i>

Phytochemical investigation of the alkaloid extract of <i>Palicourea sessilis</i> by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their structures confirmed by means of HRMS, NMR, and ECD measurements as 4-<i>N</i>-methyllyaloside (<b>3</b>), 4-<i>N</i>-methyl-3,4-dehydrostrictosidine (<b>4</b>), 4β-hydroxyisodolichantoside (<b>6</b>), and 4α-hydroxyisodolichantoside (<b>7</b>), as well as the known alkaloids alline (<b>1</b>), <i>N</i>-methyltryptamine (<b>2</b>), isodolichantoside (<b>5</b>), and 5-oxodolichantoside (<b>8</b>). In addition, the acetylcholinesterase inhibitory activity of the compounds was evaluated up to 50 μM

Targeted Isolation of Monoterpene Indole Alkaloids from <i>Palicourea sessilis</i>

Phytochemical investigation of the alkaloid extract of <i>Palicourea sessilis</i> by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their structures confirmed by means of HRMS, NMR, and ECD measurements as 4-<i>N</i>-methyllyaloside (<b>3</b>), 4-<i>N</i>-methyl-3,4-dehydrostrictosidine (<b>4</b>), 4β-hydroxyisodolichantoside (<b>6</b>), and 4α-hydroxyisodolichantoside (<b>7</b>), as well as the known alkaloids alline (<b>1</b>), <i>N</i>-methyltryptamine (<b>2</b>), isodolichantoside (<b>5</b>), and 5-oxodolichantoside (<b>8</b>). In addition, the acetylcholinesterase inhibitory activity of the compounds was evaluated up to 50 μM

A cross-platform format to associate NMR-extracted data (NMReDATA) to chemical structures

Poster presented at EUROMAR Meeting July 201

A cross-platform format to associate NMR-extracted data (NMReDATA) to chemical structures

Poster presented at SMASHNMR meeting Sep 201