115982-22-4Relevant academic research and scientific papers
Scalable Total Syntheses of Some Natural and Unnatural Lamellarins: Application of a One-Pot Domino Process for Regioselective Access to the Central 1,2,4-Trisubstituted Pyrrole Core
Kumar, Virendra,Awasthi, Annapurna,Salam, Abdus,Khan, Tabrez
, p. 11596 - 11603 (2019)
Short and scalable total syntheses of lamellarin G trimethyl ether, lamellarin D trimethyl ether, lamellarin H, lamellarin ?, dihydrolamellarin ?, and lamellarin U have been realized in four to six linear steps with an overall yield of ≤22%. Highlights of
Demethylative Lactonization Provides a Shortcut to High-Yielding Syntheses of Lamellarins
De Koning, Charles B.,Klintworth, Robin,Michael, Joseph P.
, (2020/01/31)
Modular gram-scale syntheses of the trimethyl ethers of lamellarins G (6) and D (7) were achieved from readily accessible precursors in the highest overall yields reported to date (6, six steps, 82%; 7, seven steps, 86%). A novel demethylative lactonizati
METHOD FOR PRODUCING LAMELLARIN AND DERIVATIVE THEREOF
-
, (2018/10/19)
The present application discloses a method for producing lamellarin and a derivative thereof, which is able to greatly shorten the synthesis path of the lamellarin and the derivative thereof, and to improve the yield of the lamellarin and the derivative t
Concise Synthesis of Lamellarin Alkaloids by C-H/N-H Activation: Evaluation of Metal Catalysts in Oxidative Alkyne Annulation
Mei, Ruhuai,Zhang, Shou-Kun,Ackermann, Lutz
, p. 1715 - 1718 (2017/11/27)
The performance of various transition-metal catalysts was explored in the step-economical synthesis of naturally occurring lamellarin alkaloids by C-H/N-H activation. The oxidative alkyne annulation proceeded efficiently by using sustainable ruthenium(II) catalysis, which set the stage for a concise synthesis of lamellarin D, lamellarin H and derivatives thereof.
Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D
Manjappa, Kiran B.,Lin, Jhih-Min,Yang, Ding-Yah
, p. 7648 - 7656 (2017/07/26)
An efficient construction of phenyl-substituted coumarin-pyrrole-isoquinoline-fused pentacycle via base-promoted Grob-type coupling of 3-nitrocoumarin and papaverine in a sealed tube is reported. This reaction is further applied to the total synthesis of lamellarin H in three linear steps and lamellarin D in eight linear steps with overall yields of 31% and 14%, respectively.
Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H
Lade, Dhanaji M.,Pawar, Amit B.,Mainkar, Prathama S.,Chandrasekhar, Srivari
, p. 4998 - 5004 (2017/05/12)
Total syntheses of three different lamellarins have been accomplished using a Ru(II)-catalyzed (3 + 2) annulation strategy to construct the central pyrrole ring. The striking features of this synthesis are the use of PEG-400 as a green solvent for the (3
Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H
Manjappa, Kiran B.,Syu, Jia-Ru,Yang, Ding-Yah
, p. 332 - 335 (2016/02/03)
The efficient construction of a coumarin-pyrrole-isoquinoline-fused pentacycle via the visible-light-promoted cyclization of 4-(isoquinolin-1-ylmethyl)-3-nitrocoumarin or Yb(OTf)3-catalyzed coupling of 4-chloro-3-nitrocoumarin and 1-methylisoqu
Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization
Dialer, Clemes,Imbri, Dennis,Hansen, Steven Peter,Opatz, Till
, p. 11605 - 11610 (2015/12/01)
An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
Total synthesis of lamellarins D, H, and R and ningalin B
Li, Qingjiang,Jiang, Jingqian,Fan, Aili,Cui, Yuxin,Jia, Yanxing
, p. 312 - 315 (2011/03/23)
A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)4-induced oxidative cyclization to form the lactone, and Kita's oxidation reaction to form the pyrrole-arene C-C bond.
Total synthesis and evaluation of lamellarin α 20-Sulfate analogues
Ridley, Christian P,Reddy, M. Venkata Rami,Rocha, Genalyn,Bushman, Frederic D,Faulkner
, p. 3285 - 3290 (2007/10/03)
In order to explore the influence of sulfate groups on the bioactivity profiles of marine alkaloids of the lamellarin class, three such alkaloids, lamellarin α lamellarin α 13,20-disulfate and H, were synthesized and their activities against HIV-1 integrase and cancer cell ines were compared with those of lamellarin α 20-sulfate, which is a selective inhibitor of HIV-1 integrase. Lamellarin α does not inhibit HIV-1 integrase but shows moderate cytotoxicity with good cell line selectivity. Lamellarin α13,20-disulfate is a moderate inhibitor of both HIV-1 integrase and cancer cell lines. Lamellarin H is a more potent inhibitor of HIV-1 integrase but lacked the specificity required to be medicinally useful. Copyright
