Fig. 8: Preparation of fragment 4. | Communications Chemistry

Fig. 8: Preparation of fragment 4.

From: Discovery, total syntheses and potent anti-inflammatory activity of pyrrolinone-fused benzoazepine alkaloids Asperazepanones A and B from Aspergillus candidus

Fig. 8

Reagents and conditions: a DMAP, DIPEA, EDCI, CH2Cl2, 0 °C to RT, 12 h, 90%; b LiHMDS, THF, −20 °C to RT, 6 h, 70%; c TFA/MeCN (1: 10), reflux, 8 h; d 5, AcOH/EtOH (1: 10), 70 °C, 12 h, 30% over two steps; e LiOH, MeOH/H2O (1: 1), RT, 2 h, 85%. DMAP 4-dimethylaminopyridine, DIPEA diisopropylethylamine, EDCI 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, LiHMDS lithium hexamethyldisilazide. TFA trifluoroacetic acid, THF tetrahydrofuran, RT room temperature.

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