69778-83-2Relevant articles and documents
SYNTHESIS OF PUKELEIMIDE A
James, Gwyn D.,Pattenden, Gerald,Mills, Stuart D.
, p. 3617 - 3620 (1985)
A total synthesis of the 5-ylidenepyrrole-2-one pukeleimide A (3), a constituent of the marine blue-green alga Lyngbya majuscula,is described.
Metal-Free and Versatile Synthetic Routes to Natural and Synthetic Prodiginines from Boron Dipyrrin
Li, Jin,Zhang, Qian,Yin, Jian,Yu, Changjiang,Cheng, Kai,Wei, Yun,Hao, Erhong,Jiao, Lijuan
, p. 5696 - 5699 (2016)
Prodiginines, as a family of bacterial alkaloids, possess a number of interesting biological activities. New, concise synthetic routes for the facile preparation of both synthetic and natural prodiginines in good yields have been developed, which use BODIPY functionalization reactions, such as condensation, nucleophilic substitution, and BF2 deprotection. This new metal-free synthetic method opens the door toward a wide variety of C-ring functionalized prodiginines, including those that are not possible to obtain through current synthetic methods, for their advanced biological activities.
Synthesis of gallinamide A analogues as potent falcipain inhibitors and antimalarials
Conroy, Trent,Guo, Jin T.,Elias, Nabiha,Cergol, Katie M.,Gut, Jiri,Legac, Jennifer,Khatoon, Lubna,Liu, Yang,McGowan, Sheena,Rosenthal, Philip J.,Hunt, Nicholas H.,Payne, Richard J.
supporting information, p. 10557 - 10563 (2015/02/19)
Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.
Preparation and intramolecular [2+2]-photocycloaddition of 1,5-dihydropyrrol-2-ones and 5,6-dihydro-1H-pyridin-2-ones with C-, N-, and O-linked alkenyl side chains at the 4-position
Albrecht, Dominik,Basler, Birte,Bach, Thorsten
, p. 2345 - 2356 (2008/09/19)
(Chemical Equation Presented) The 1,5-dihydropyrrol-2-ones 2, 6, 9, and 11 were prepared from methyl tetramates (1a-c), N-Boc-protected tetramic acid (3), or N-Boc-protected tetramic acid bromide (7) in short reaction sequences and in very good overall yields. The homologous 5,6-dihydro-1H-pyridin-2-ones 16,18, 20, 21, 23, and 27 were prepared along analogous routes starting from piperidin-2,4-dione (19) or from its N-terf-butyl derivative 15. Optimized conditions for the [2+2]-photocycloaddition include the use of dichloromethane as the solvent and an irradiation with a mercury low-pressure lamp (λ = 254 nm). Upon applying these conditions at ambient temperature, the corresponding intramolecular photocycloaddition products 28-37 were obtained in good yields (52-79%) and with perfect diastereoselectivity. The constitution and configuration of the products was elucidated by NMR-spectroscopy. For the O-tethered substrates 2a and 20, a strong decrease of the photocycloaddition rate with temperature was observed. The effect was less pronounced for N- and C-tethered substrates 6, 9, 23, and 27. The use of a chiral complexing agent to achieve enantioselective reactions appears viable. Complexing agent (-)-38, however, is not suited because of its instability at λ = 254 nm.
Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors
Sartori, Andrea,Curti, Claudio,Battistini, Lucia,Burreddu, Paola,Rassu, Gloria,Pelosi, Giorgio,Casiraghi, Giovanni,Zanardi, Franca
experimental part, p. 11697 - 11705 (2009/04/06)
The direct Mukaiyama-Michael addition of vinylogous tetramate donors to a number of different Michael acceptors has been easily executed, by employing the TMSOTf/Et3N mixture as soft Lewis acid/base promoter agent. Richly functionalized, highly
Total Synthesis of Pukeleimide A, a 5-Ylidenepyrrol-2(5H)-on e from Blue Green Algae
James, Gwyn D.,Mills, Stuart D.,Pattenden, Gerald
, p. 2581 - 2584 (2007/10/02)
A total synthesis of pukeleimide A 5, a member of a rare family of naturally occuring 5-ylidenepyrrol-2(5H)-ones produced by the marine blue alga Lyngbya majuscula, is described.The synthesis is based on elaboration of the ylidenepyrrolone 11a from the maleimide 13a by a regio- and stereo-selective Wittig reaction with ethoxycarbonylmethylene(triphenyl)phosphorane, followed by conversion of 11a into the amide 25, and oxidation of 25 with selenium dioxide.
Methyl (E)-4-chloro-3-methoxy-2-butenoate: An extremely versatile four carbon building block
Duc,McGarrity,Meul,Warm
, p. 391 - 394 (2007/10/02)
Methyl (E)-4-chloro-3-methoxy-2-butenoate (3a) is inexpensively prepared from methyl 4-chloroacetoacetate using thionyl chloride and methanol on an industrial scale. Many nucleophilic substitution reactions of chloride, which are impossible with the unpro
Process for the production of 4-alkoxy-3-pyrrolin-2-ones
-
, (2008/06/13)
Process for the production of 4-alkoxy-3-pyrrolin-2-ones, which are preferred intermediate products for the production of cerebrally-active pharmaceutical products.
Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters
-
, (2008/06/13)
4-Alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters are intermediate products for the production of cerebrally-active pharmaceutical products. The advantageous process for production of the new intermediate products is described.
SYNTHESIS OF 5-SUBSTITUTED 4-O-METHYL TETRAMATES
Jones, Raymond C.F,Bates, Andrew D.
, p. 5285 - 5288 (2007/10/02)
4-Methoxy-Δ3-pyrrolin-2-ones (4-O-methyl tetramates) are alkylated at C-5 via a lithio-derivative; an N-substituent may be introduced either during or after heterocycle formation.
