144398-24-3Relevant academic research and scientific papers
Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues
Liou, Teau-Jiuan,Satyanarayana, Iddum,Yang, Ding-Yah
, p. 43168 - 43174 (2020/12/18)
Three lamellarin alkaloids type III (lamellarin R, lukianol A and lamellarin O) were synthesized using the Barton-Zard reaction as a key step to construct the central pyrrole core. Some of their corresponding 4-benzoyl and 5-phenyl substituted pyrrole ana
Convergent Total Synthesis of Lamellarins and Their Congeners
Morikawa, Daiki,Morii, Kazuki,Yasuda, Yuto,Mori, Atsunori,Okano, Kentaro
, p. 8603 - 8617 (2020/07/16)
A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β′-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.
Total synthesis of the marine natural products lukianols A and B
Takamura, Kaoru,Matsuo, Hisami,Tanaka, Ayana,Tanaka, Junji,Fukuda, Tsutomu,Ishibashi, Fumito,Iwao, Masatomo
, p. 2782 - 2788 (2013/03/29)
Total synthesis of the pyrrolic marine natural products lukianols A (1) and B (2) has been achieved using N-benzenesulfonyl-3,4-dibromopyrrole (3) as a common starting material. The key synthetic strategy developed is the combined bromine-directed lithiation and palladium-catalyzed cross-coupling of 3 to produce 3,4-diarylpyrrol-2-carboxylates. Regioselective iodination of the phenolic intermediate 24 was thoroughly investigated for the synthesis of lukianol B.
Biomimetic syntheses of lamellarin and lukianol-type alkaloids
Peschko, Christian,Winklhofer, Christian,Terpin, Andreas,Steglich, Wolfgang
, p. 3048 - 3057 (2008/02/08)
The formation of 3,4-diarylpyrrole-2,5-dicarboxylic acids from arylpyruvic acids and 2-arylethylamines was used as a key step for the synthesis of several marine pyrrole alkaloids. The utility of this method is illustrated through the development of synth
Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A
Liu, Jian-Hui,Yang, Qing-Chuan,Mak, Thomas C. W.,Wong, Henry N. C.
, p. 3587 - 3595 (2007/10/03)
A combined use of α-lithiation and nucleophilic substitutions of N,N- dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the β-effect of a trimethylsilyl group, a highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles 23 and 34 was accomplished. The marine natural product lukianol A (3) was prepared utilizing this strategy.
Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels - Alder reactions
Boger, Dale L.,Boyce, Christopher W.,Labroli, Marc A.,Sehon, Clark A.,Jin, Qing
, p. 54 - 62 (2007/10/03)
Concise, efficient total syntheses of ningalin A (1), lamellarin O (2), lukianol A (3), and permethyl storniamide A (5) are detailed on the basis of a common heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole cores found in the three classes of marine natural products. Examination of the natural products and a number of synthetic intermediates revealed that some including lamellarin O (2) and lukianol A (3) exhibit modest cytotoxic activity against both wild-type and multidrug- resistant tumor cell lines. Fundamentally more important, a new class of agents including permethyl storniamide A (5) and its precursor 30, which lack inherent cytotoxic activity, are disclosed which reverse the multidrug- resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.
