36193-36-9Relevant academic research and scientific papers
Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F
Dagoneau, Dylan,Xu, Zhengren,Wang, Qian,Zhu, Jieping
, 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.
Catalytically Asymmetric Pd/Norbornene Catalysis: Enantioselective Synthesis of (+)-Rhazinal, (+)-Rhazinilam, and (+)-Kopsiyunnanine C1-3
Zhao, Kun,Xu, Shibo,Pan, Chongqing,Sui, Xianwei,Gu, Zhenhua
supporting information, p. 3782 - 3785 (2016/08/16)
A catalytically asymmetric palladium/norbornene-catalyzed reaction is reported, where α-aryl tetrahydroquinoline derived phosphoramidite L15 is found to be the optimum ligand. Taking advantage of this transformation, the concise and unified enantioselective syntheses of (+)-rhazinal, (+)-rhazinilam, and (+)-kopsiyunnanine C1, C2, and C3 are realized.
Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: Application to the total synthesis of (±)-rhazinilam
Su, Youla,Zhou, Haipin,Chen, Jiaxuan,Xu, Jinyi,Wu, Xiaoming,Lin, Aijun,Yao, Hequan
, p. 4884 - 4887 (2015/04/27)
A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.
Biosynthetically inspired divergent approach to monoterpene indole alkaloids: Total synthesis of mersicarpine, leuconodines b and d, leuconoxine, melodinine e, leuconolam, and rhazinilam
Yang, Yang,Bai, Yu,Sun, Siyuan,Dai, Mingji
, p. 6216 - 6219 (2015/02/19)
Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.
Chemical synthesis of aspidosperma alkaloids inspired by the reverse of the biosynthesis of the rhazinilam family of natural products
McMurray, Lindsay,Beck, Elizabeth M.,Gaunt, Matthew J.
, p. 9288 - 9291 (2012/10/30)
Pyrrole reduction: Iterative metal-catalyzed C-H functionalization reactions facilitated the preparation of a highly substituted pyrrole derivative. This derivative could be transformed into the pyrrole-containing secondary metabolite, rhazinilam, which could in turn be transformed through a reductive transannular cascade process into the structurally complex pyrrolidine-containing alkaloid natural product, aspidospermidine.
Total synthesis of rhazinilam: Axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization
Gu, Zhenhua,Zakarian, Armen
supporting information; experimental part, p. 4224 - 4227 (2010/11/17)
Figure Presented. A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.
Au(I)-catalyzed annulation of enantioenriched allenes in the enantioselective total synthesis of (-)-rhazinilam
Liu, Zuosheng,Wasmuth, Andrew S.,Nelson, Scott G.
, p. 10352 - 10353 (2007/10/03)
Highly stereoselective Au(I)-catalyzed pyrrole additions to enantioenriched allenes afford a unique entry to optically active heterocycles. Asymmetric quaternary carbons can be installed with concurrent heterocycle annulation utilizing this methodology. The enantioenriched allenes are conveniently obtained by catalytic asymmetric acyl halide-aldehyde cyclocondensations and SN2′ ring opening of the resulting enantioenriched β-lactones. An enantioselective total synthesis of (-)-rhazinilam highlights the potential utility of this reaction technology in target-oriented synthesis. Copyright
Concise synthesis of (±)-Rhazinilam through direct coupling
Bowie Jr., Alfred L.,Hughes, Chambers C.,Trauner, Dirk
, p. 5207 - 5209 (2007/10/03)
(Chemical Equation Presented) A concise synthesis of rhazinilam through direct, palladium-catalyzed, intramolecular coupling is described.
Concise synthesis of (±)-rhazinilam
Magnus, Philip,Rainey, Trevor
, p. 8647 - 8651 (2007/10/03)
2-Piperidone has been converted into (±)-rhazinilam in nine steps in 8% overall yield. The key transformation involves the conversion of the lactam 5 into the annulated pyrrole derivative 3 via the thiophenyl imine 8.
