127733-22-6Relevant academic research and scientific papers
Synthesis of brassinolide and its biosynthetic precursors using methyl 3-hydroxy-2-methylpropionate
Khripach,Zhabinskii,Parkhimovich,Gulyakevich
experimental part, p. 240 - 249 (2010/04/26)
Formal synthesis of plant hormones that belong to the group of 24α-methylbrassinosteroids, including brassinolide and its biosynthetic precursors with one hydroxyl group in their side chain, was performed. Stereochemistry of a methyl group at the C24 atom
Stereocontrolled and convergent total synthesis of amphidinolide T3
Deng, Li-Sheng,Huang, Xiao-Ping,Zhao, Gang
, p. 4625 - 4635 (2007/10/03)
Stereocontrolled and convergent total synthesis of amphidinolide T3 has been described. A retrosynthetic scheme was constructed that led to the recognition of readily available and enantiomerically related compounds as starting materials for the total synthesis of amphidinolide T3. Thus, the two key building blocks 6 and 7 were defined as subtargets and synthesized in optically active forms. The C1-C12 fragment 6 was derived from commercially available D-glutamic acid or its synthetically equivalent (R)-5- hydroxymethyltetrahydrofuran-2-one 16 as starting material involving highly diastereoselective asymmetric allylation as a key step. The C13-C21 fragment 7 was efficiently synthesized in high yield through the dithiane coupling of the segment 10 and iodide 11, followed by subsequent deprotection and Petasis olefination. Eventually, assembly of the fragment aldehyde 6 and dithiane 7 along with C-C bond formation, a two-step oxidation-reduction sequence, selective macrolactonization, and functional transformation furnished the convergent total and formal synthesis of amphidinolide T3 and T4, and this approach also provides a flexible and practical synthesis of amphidinolide T macrolides.
Transformation of esters into 2-substituted allyl halides via tertiary cyclopropanols: Application in the stereoselective synthesis of (2S,3S,7S)-3,7-dimethyl-2-pentadecyl acetate, the sex pheromone of the pine sawfly Neodiprion sertifer
Bekish, Andrei V.,Prokhorevich, Konstantin N.,Kulinkovich, Oleg G.
, p. 5069 - 5075 (2007/10/03)
(2S,3S,7S)-3,7-Dimethyl-2-pentadecyl acetate (ac-1), the sex pheromone of the pine sawfly Neodiprion sertifer, has been newly synthesized by the transformation of the corresponding esters 8 and 12 into 2-oxyalkyl-substituted allyl bromides 4 and 5 via ter
Synthetic study of tautomycin. Part 2: Synthesis of Ichihara's fragment based on regioselective enzymatic acetylation of complex molecule
Ishii, Yusuke,Nagumo, Shinji,Arai, Takayuki,Akuzawa, Masami,Kawahara, Norio,Akita, Hiroyuki
, p. 716 - 725 (2007/10/03)
Formal synthesis of tautomycin, which inhibits type 1 and type 2A protein phosphatases, was achieved. Spiroketal diol 21 was synthesized from alcohol 2 or 11. The regioselective enzymatic acetylation of 21 with the lipase 'Amano PS' gave monoacetate 23 in
Total Synthesis of (+)-Latrunculin A, an Ichthyotoxic Metabolite of the Sponge Latrunculia magnifica, and Its C-15 Epimer
White, James D.,Kawasaki, Motoji
, p. 5292 - 5300 (2007/10/02)
Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach.Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, β-keto ester 27, and phosphonium salt 26, which established the conjugated E,Z-diene moiety of 31.The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection.Final lactonization of 47 was carried out using the Mitsunobu protocol.A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.
