Front Cover: Stereodivergent Diversity‐Oriented Synthesis: Exploiting the Versatility of 2‐Piperidine Ethanol (Eur. J. Org. Chem. 25/2019)

Abstract

The Front Cover shows a playful representation of the fascination to explore, that always moved science forward. In particular, the exploration of the Chemical Space is a challenging experience that excites creativity and enthusiasm of the organic chemists. The 2‐piperidine ethanol appears as a kite in the hands of a bold researcher to give vent to the imagination, looking for new structures and landing on known chemical entities. More information can be found in the Full Paper by D. Passarella et al.

Brown Allylation: Application to the Synthesis of Natural Products

“…The configuration of the product depends on (Z)-or (E)configuration of the crotyl group, which may preferentially furnish syn or anti adduct, respectively (Scheme 4). [20] The conditions of the Brown crotylation are similar to those of the allylation. However, in case of crotylation, it is even more important to prepare the (Ipc) 2 B-crotyl reagents in situ, as they can easily isomerize during storage via borotropic rearrangement (Figure 2).…”

“…= 84 %). [20] Dysoxylactam A ( 14) is a novel macrocyclolipopeptide, isolated from the bark of a Chinese plant named Dysoxylum hongkongense. This natural product acts as a potent multi-drug resistance reverser, able to significantly inhibit P-gp in cancer cells.…”

“…Each of the diastereomers then underwent Mitsunobu reaction, acylation and RCM, after which either intramolecular aza-Michael addition was applied to obtain compound 23 or Eschweiler-Clarke conditions to produce 24 or 25. [20]…”

“…[4,[12][13][14][15][16][17][18] As Brown allylation is one of the most applied procedures and has been also the one utilized by our research group, it has served as an inspiration for this review. [19,20] Here, we provide the comprehensive overview of the reaction conditions and mechanism and emphasize the application of Brown allylation in natural product chemistry. Moreover, the relevant data regarding Brown crotylation have been included.…”