Total synthesis of (±)-rocaglamide and some aryl analogues

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

“…[209] In the synthesis of the carbazole natural product murrastifoline A Chida brought about the double N-arylation [168,169] of primary amine 121 with 2,2'-dihalobiphenyl 120 as a key step (Scheme 51). [170] During construction of a library of natural product-like diketopiperazines for biological screening Porco and Panek at Boston University used ligand 1 in coupling morpholine with the complex aryl bromide 123 (Scheme 52).…”

Use of natural products in the crop protection industry

“…Extraction of 500 kg of stem bark delivered only 110 mg of rocaglamide (27). However, a robust total synthesis was developed which allowed the preparation of several non-natural analogues and provided an insight into the structureactivity relationship (Dobler et al 2001). It could be demonstrated that only limited structural variations were possible without losing insecticidal activity.…”

Palladium‐Catalyzed Aromatic Carbon–Nitrogen Bond Formation

“…Researchers at Novartis performed the arylation of aliphatic N-heterocycles with the complex aryl bromide 43 toward the synthesis of analogs 44 of the insecticidal natural product rocaglamide (Scheme 13.48) [103]. Cs 2 CO 3 acted as mild base to prevent side reactions and epimerization.…”