Syntheses based on β-phenylethylamines VI. Synthesis and mass-spectrometric properties of bis-β-phenylethylbenzylamines and the products of their methylation

Concise Total Synthesis of Aplysinellamides A and B

“…Intermediates including methyl N α -Boc-D-lysinate 9 and the cinnamic acids 11 and 16 were synthesised according to reported literature procedures. [13][14][15][16][17][18] Accordingly, D-lysine (5) was reacted with ClCOOBn in the presence of CuSO 4 to form D-lys(Z)-OH 6 in 91% yield, followed by N-protection with (Boc) 2 O to afford acid 7 in 96% yield. 13 Acid 7 was alkylated with CH 3 I smoothly and gave methyl ester 8 in 85% yield.…”

“…Veratraldehyde was mono-brominated with Br 2 /AcOH to give 3-bromo-4-methoxybenzaldehyde 10 in 70% yield, which was subjected to Doebner-Knoevenagel condensation with malonic acid in the presence of pyridine and piperidine to afford cinnamic acid 11 in 92% yield. 15,16 Similarly, 4-hydroxybenzaldehyde was dibrominated to afford…”