1316859-98-9Relevant academic research and scientific papers
Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F
Dagoneau, Dylan,Xu, Zhengren,Wang, Qian,Zhu, Jieping
supporting information, p. 760 - 763 (2016/02/27)
A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chloride to give tetrahydroindolizine 6 and dioxopyrrole 7, respectively. The former was converted into (-)-rhazinilam, while the latter was converted into (-)-leucomidine B and (+)-leuconodine F. A substrate-directed highly diastereoselective reduction of a sterically unbiased double bond by using a homogeneous palladium catalyst was developed. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B. Be divergent: Concise total syntheses of (-)-rhazinilam, (-)-leucomidine B, and (+)-leuconodine F were accomplished from the common intermediate A. A homogeneous palladium catalyst was exploited for the first time to accomplish a substrate-directed highly diastereoselective hydrogenation of a sterically unbiased double bond. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B.
Unified strategy to monoterpene indole alkaloids: Total syntheses of (±)-Goniomitine, (±)-1,2-Dehydroaspidospermidine, (±)-Aspidospermidine, (±)-Vincadifformine, and (±)-Kopsihainanine A
Wagnires, Olivier,Xu, Zhengren,Wang, Qian,Zhu, Jieping
supporting information, p. 15102 - 15108 (2014/12/11)
Total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A were achieved featuring two common key steps: (1) a palladium-catalyzed decarboxylative vinylation that provides quick access to cyclopentene intermediates containing all of the carbons present in the natural products and (2) an integrated oxidation/reduction/cyclization (iORC) sequence for skeletal reorganization that converts the cyclopentenes to the pentacyclic structures of the natural products. By incorporation of a geometric constraint to iORC substrates, both the chemoselectivity (C7 vs N1 cyclization) and the stereoselectivity (trans- vs cis-fused ring system) of the cyclization process can be controlled.
Palladium-catalyzed decarboxylative vinylation of potassium nitrophenyl acetate: Application to the total synthesis of (±)-goniomitine
Xu, Zhengren,Wang, Qian,Zhu, Jieping
supporting information, p. 3272 - 3276 (2013/04/10)
Merge and divert: The natural product (±)-goniomitine was synthesized by a method featuring two key steps: 1) fragment coupling to a functionalized cyclopentene by a novel palladium-catalyzed decarboxylative vinylation reaction and 2) an unprecedented one-pot integrated oxidation/reduction/cyclization (IORC) process to convert the substituted cyclopentene into the tetracyclic skeleton of goniomitine with high chemo-, regio-, and diastereoselectivity.
Palladium-catalyzed decarboxylative coupling of potassium nitrophenyl acetates with aryl halides
Shang, Rui,Huang, Zheng,Chu, Ling,Fu, Yao,Liu, Lei
supporting information; experimental part, p. 4240 - 4243 (2011/10/09)
A palladium-catalyzed decarboxylative cross-coupling of potassium 2- and 4-nitrophenyl acetates with aryl chlorides and bromides has been developed. Because the nitro group can be readily converted to many other functional groups, the new reaction provides a useful method for the preparation of diverse 1,1-diaryl methanes and their derivatives.
