149378-57-4Relevant academic research and scientific papers
Gaining diversity in solid-phase synthesis by modulation of cleavage conditions from hydroxymethyl-based supports. Application to lamellarin synthesis
Cironi, Pablo,Cuevas, Carmen,Albericio, Fernando,álvarez, Mercedes
, p. 8669 - 8675 (2004)
The application of a number of Lewis acids as a cleavage/deprotection method in the solid-phase synthesis of organic molecules can render several analogues, which, after purification, can be submitted for biological evaluation.
Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling
Mori, Atsunori,Morii, Kazuki,Morikawa, Daiki,Okano, Kentaro,Yasuda, Yuto
, p. 13388 - 13401 (2021/10/12)
A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at -78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide in the presence of catalytic palladium to provide the fully substituted pyrrole. Subsequent halogen-lithium exchange was performed to incorporate a boronate group exclusively at the β position proximal to the ester moiety. This synthetic intermediate allowed stepwise diarylation for the total synthesis of lamellarins G, J, L, and Z.
Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates
Komatsubara, Masashi,Umeki, Teppei,Fukuda, Tsutomu,Iwao, Masatomo
, p. 529 - 537 (2014/04/03)
A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert- butoxycarbonyl)-1Hpyrrole (1) followed
Total synthesis of lamellarins D, L, and N
Fujikawa, Naotaka,Ohta, Takeshi,Yamaguchi, Tomohiro,Fukuda, Tsutomu,Ishibashi, Fumito,Iwao, Masatomo
, p. 594 - 604 (2007/10/03)
Total synthesis of cytotoxic marine alkaloids, lamellarins D, L, and N, has been achieved by using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki-Miyaura coupling of the 3,4-dihydroxypyrrole bistriflate 6 as the key reactions. The total yields of lamellarins D, L, and N from the common intermediate 6 are 54, 58, and 50%, respectively.
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.
A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
Ploypradith, Poonsakdi,Mahidol, Chulabhorn,Sahakitpichan, Poolsak,Wongbundit, Siriporn,Ruchirawat, Somsak
, p. 866 - 868 (2007/10/03)
Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields fro
Biomimetic total synthesis of lamellarin L by coupling of two different arylpyruvic acid units
Peschko, Christian,Winklhofer, Christian,Steglich, Wolfgang
, p. 1147 - 1152 (2007/10/03)
Reaction of the ethyl 3-arylpyruvate 5a with the methyl 2-bromo-3-arylpyruvate 6b in the presence of the 2-arylethylamine 4 afforded the pyrrole derivative 10, which could be transformed into lamellarin L (1) in five steps. The synthesis proceeds with 38%
