97614-65-8Relevant academic research and scientific papers
Synthesis of lamellarin alkaloids using orthoester-masked α-keto acids
Shirley, Harry J.,Koyioni, Maria,Muncan, Filip,Donohoe, Timothy J.
, p. 4334 - 4338 (2019/04/17)
Pyruvic acid and other α-keto acids are frequently encountered as intermediates in metabolic pathways, yet their application in total synthesis has met with limited success. In this work, we present a bioinspired strategy that utilizes highly functionaliz
METHOD FOR PRODUCING LAMELLARIN AND DERIVATIVE THEREOF
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Paragraph 0122; 0125, (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
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
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.
Synthesis of lamellarins via regioselective assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-one core
Fukuda, Tsutomu,Katae, Takatoshi,Harada, Issei,Iwao, Masatomo
, p. 950 - 971 (2017/07/28)
A modular synthesis of lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano- [3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol- 4(3H)-one core and the appropriate arylb
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.
Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug Likeness and Biological Activities
Theppawong, Atiruj,Ploypradith, Poonsakdi,Chuawong, Pitak,Ruchirawat, Somsak,Chittchang, Montakarn
, p. 2631 - 2650 (2016/02/09)
With the goal to improve the aqueous solubility of lamellarins, the lactone ring in their skeleton was replaced with a lactam moiety in azalamellarins. However, the reported synthetic route produced such derivatives in very low yields. Hence, this study focused on developing an efficient simplified total synthetic scheme that could furnish both azalamellarins and the parent lamellarins from the same pyrrole ester intermediates. Subsequent comparative profiling revealed that the introduced lactone-to-lactam replacement rendered these molecules less lipophilic, whereas their cancer cytotoxicity remained equipotent to that of the parent compounds. Interestingly, their inhibitory activity was significantly enhanced towards the multifaceted GSK-3β enzyme. Our results clearly demonstrate the therapeutic potential of this promising class of marine-derived natural products and justify their further development, especially into anticancer agents.
Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents
Shen, Li,Xie, Nan,Yang, Bo,Hu, Yongzhou,Zhang, Yongmin
, p. 807 - 817 (2014/10/15)
Enlightened by the modification route from Camptothecin (CPT) to Topotecan and based on classical drug design theory, a series of Mannich derivatives of lamellarin D were designed and synthesized in 26-27 steps starting from vanillin and isovanilin. All synthesized compounds were then biologically evaluated for their in vitro anti-cancer activities and Topo I inhibitory activities. The results showed that most target compounds exhibited Topo I inhibitory activities in equivalent level with that of lamellarin D. Compound SL-9 exhibited better Topo I inhibitory activity than that of lamellarin D. Compounds SL-2, SL-3, SL-4, SL-5 and SL-11 exhibited better anti-proliferative activity against HT-29 cells than that of lamellarin D.
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 of natural and unnatural lamellarins with saturated and unsaturated D-rings
Ploypradith, Poonsakdi,Petchmanee, Thaninee,Sahakitpichan, Poolsak,Litvinas, Nichole D.,Ruchirawat, Somsak
, p. 9440 - 9448 (2007/10/03)
(Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.
