Total synthesis of fluvirucinine A1

Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis

“…On the other hand, the synthesis of segment 365 was started with compound 361, synthesized as reported previously. 252 Reaction of alcohol 362 (provided in three steps from 361), with triphenylphosphine in the presence of iodine and imidazole in THF gave the corresponding allyl iodide, which upon Evans' alkylation 253 with N-propionyl oxazolidinone gave 363 in good yield as a single isomer as conrmed by analysis of the 1 H or 13 was obtained in 71% yield over two steps. Aer several steps, the desired natural product 359 was obtained (Scheme 69).…”

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

“…Thus, in target synthesis of biologically active macroheterocycles, after the stage of the formation of unsaturated cycles, the reaction of reduction of multiple bonds follows: exhaustive hydrogenation of C≡C, C=C and C=N bonds over Wilkinson's catalyst, Raney nickel and Pd/C, [6][7][8][9][10][11] reduction of C=N bonds using NaBH 4 or LiAlH 4 [6][7][8][9][10][11][12] and partial hydrogenation of the C-C triple bond to Z-double over Lindlar catalyst [13][14][15][16][17][18] that allow obtaining both isolated bonds, and conjugated systems.…”

Synthesis of Fluvirucins and Their Aglycons, the Fluvirucinins

“…In 2011, Radha Krishna reported 17 an enantioselective synthesis of fluvirucinin A 1 involving the same C 4 -C 5 bond disconnection. Closure of the macrocyclic ring was also achieved by RCM reaction, in this case from diene 35, which was prepared in nearly quantitative yield by amidation between carboxylic acid 33 and amine 34 (C 1 -C 4 and C 5 -N fragments of fluvirucinin A 1 ).…”