Matthias Treu

Synthesis of (±)-6H-benzofuro[3a,3,2,ef][3]benzazepine: an unnatural analog of (−)-galanthamine

Abstract The first total synthesis of an unnatural analog of the anti-Alzheimer drug (−)-galanthamine has been accomplished using K3[Fe(CN)]6 in the key step to build up the heterocyclic ring system via an oxidative tandem cyclization.

Synthesis and stereoselective dealkylation of N-chiral quarternary N-alkyl galanthaminium halides

The synthesis of N-chiral galanthaminium halides and their stereoselective dealkylation is described. The stereochemistry of two key compounds was determined by X-ray structure analysis.

4a,5,9,10,11,12-Hexahydro-6H-benzo[a]cyclohepta[hi]benzofuran - Synthesis of Unnatural Galanthamine Analogs

The synthesis of an unnatural galanthamine analog is reported.

An Improved Synthesis of 5-(2,6-Dichlorophenyl)-2-(phenylthio)-6H-pyrimido[1,6-b]pyridazin-6-one (a VX-745 analog)

An improved procedure for the synthesis an analog of the p38 inhibitor compound VX- 745 is reported.

Bidirectional Conversion of Galanthamine and Crinine Type Heterocycles

The conversion of galanthamine-type molecules into crinine-type compounds and vice versa has been accomplished by a ring opening-Michael addition-cascade of a galanthamine-type secondary amine and a crinine-type quarternary ammonium salt.

Synthesis of Precursors for the Oxidative Tandem Cyclization of Diphenols to Galanthamine Analogs

Methods for the preparation of 4-bromo-5-[2-(4-hydroxybenzyl)benzyl]-2-methoxyphenol and 4-bromo-5-[4-(4-hydroxyphenyl)butyl]-2-methoxyphenol are described.

Preparation of Shortened Norbelladine Analogs

The preparation of N-[(2-bromo-5-hydroxy-4-methoxyphenyl)methyl]-N-[(4-hydroxyphenyl)methyl]formamide (5) and 2-bromo-5-hydroxy-α-[(4-hydroxyphenyl)methyl]-4-methoxypropaneamide (10) is reported.

(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol (Norsanguinine)

Norsanguinine (2) is an alkaloid isolated from the bulbs of L. sanguinea [1] and synthesized as racemate by Kita [2].[...]

2-(2-Bromophenyl)-1-(4-methoxyphenyl)ethanone

To anhydrous AlCl3 (27.35 g, 205 mmol) and anisole (24.11 g, 223 mmol) in dry chloroform (300 mL) 2-bromobenzeneacetyl chloride [1] (43.4 g, 186 mmol) in dry chloroform (100 mL) was added over 30 min at 0 °C and stirred at ambient temperature for 15 h.[...]

2-[2-[2-Bromo-4-methoxy-5-(1-methylethoxy)phenyl]-1-oxoethyl]-2-[4-(1-methylethoxy)phenylmethyl]propanedioic Acid Dimethyl Ester

To a suspension of NaH (685 mg, 15.7 mmol, 55% in oil, purified by trituration with dry petroleum ether (3 x30 mL)) in dry THF (30 mL) [[4-(1-methylethoxy)phenyl]methyl]propanedioic acid dimethyl ester [1] (4.00g, 14.3 mmol) in dry THF (10 mL) was added at 0 °C and stirred for 1 h at ambient temperature. 2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetyl chloride [2] (4.59 g, 14.3 mmol) in dry THF (10 mL) was addedand stirred for 24 h at ambient temperature. Satd. NH