Metal catalysed versus organocatalysed stereoselective synthesis: The concrete case of myrtucommulones

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

“…As an answer to the rising interest for pharmaceutical applications of myrtucommulones and related compounds, in the last decade several independent approaches have been developed in order to synthesize compounds belonging to this class. In particular, myrtucommulone A was first obtained from commercially available precursors [61], and later through stereoselective synthesis [62,63]. Other analogs of the series have been synthetically obtained (Table 2), particularly in the last couple of years, which possibly preludes further achievements in this respect in the short term.…”

Recent advances in the synthesis of natural products containing the phloroglucinol motif

“…80 Despite multiple attempts, the metal-catalysed synthesis did not show promising diastereoselectivity, prompting Jauch towards organocatalysis. 81 Under the inuence of cinchonidine (103), coupling of 34 with 4.4 equivalents of 63 afforded myrtucommulone A, predominantly in a meso-form (82% de).…”

“…80 with 53, leaving the nal Vilsmeier-Haack formylation to afford acrofolional(81).Wang presented the total synthesis of baeckenon B (84, Scheme 14), 67 a natural dimeric phloroglucinol isolated from the leaves of Baeckea frutescens with moderate antibacterial activity against Bacillus subtilis.…”