325172-29-0Relevant academic research and scientific papers
Total Synthesis of (-)-Citreoisocoumarin, (-)-Citreoisocoumarinol, (-)-12-epi-Citreoisocoumarinol, and (-)-Mucorisocoumarins A and B Using a Gold(I)-Catalyzed Cyclization Strategy
Mallampudi, N. Arjunreddy,Choudhury, Utkal Mani,Mohapatra, Debendra K.
, p. 4122 - 4129 (2020)
A unified and concise first asymmetric total synthesis of (-)-citreoisocoumarin (2), (-)-citreoisocoumarinol (3), 12-epi-citreoisocoumarinol (4), and (-)-mucorisocoumarins A (5) and B (6) have been accomplished from the common intermediate (-)-6-O-methyl-
Design and synthesis of pironetin analogue/combretastatin A-4 hybrids and evaluation of their cytotoxic activity
Torijano-Gutierrez, Sandra,Vilanova, Concepcion,Diaz-Oltra, Santiago,Murga, Juan,Falomir, Eva,Carda, Miguel,Marco, J. Alberto
, p. 2284 - 2296 (2014)
We describe the preparation of a series of hybrid molecules containing a combretastatin A-4 moiety and a pironetin analogue fragment linked by an ester spacer of variable length. The cytotoxic activities of these compounds have been measured and the relationship between the structure and cytotoxicity is discussed. Some of the tested compounds showed cytotoxicity values of the same order of magnitude as those of the parental molecules, combretastatin A-4 and pironetin, and were less toxic than the latter for normal cells. The preparation of a series of hybrid molecules containing a combretastatin A-4 moiety and a pironetin analogue fragment linked by a spacer of variable length is described. The relationship between structure and cytotoxicity is discussed. Cytotoxicity values of some compounds were similar to those of the parent molecules, combretastatin A-4 and pironetin, and some were less toxic than the latter for normal cells. Copyright
Byproduct formation during the biosynthesis of spinosyn A and evidence for an enzymatic interplay to prevent its formation
Choi, Sei-hyun,Franklin, Joseph Livy,Huang, Teng-Yi,Hung, Shang-Cheng,Jeon, Byung-sun,Kim, Namho,Liu, Hung-wen,Ruszczycky, Mark W.
supporting information, (2021/11/30)
Biosynthesis of spinosyn A in Saccharopolyspora spinosa involves a 1,4-dehydration followed by an intramolecular [4 + 2]-cycloaddition catalyzed by SpnM and SpnF, respectively. The cycloaddition also takes place in the absence of SpnF leading to questions
Stereoselective synthesis of dendrodolide-L
Bujaranipalli, Sheshurao,Das, Saibal
, p. 254 - 260 (2017/03/01)
An efficient stereoselective total synthesis of 12-membered macrolide dendrodolide L has been achieved. The key reactions involved are Keck asymmetric allylation, Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu reaction and ring-closing metathesis reaction.
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells
Mohapatra, Debendra K.,Reddy, D. Sai,Janaki Ramaiah,Ghosh, Sowjanya,Pothula, Vikram,Lunavath, Swetha,Thomas, Shine,Pushpa Valli,Bhadra, Manika Pal,Yadav, Jhillu S.
, p. 1389 - 1396 (2014/03/21)
Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast can
A reductive coupling strategy towards ripostatin A
Schleicher, Kristin D.,Jamison, Timothy F.
supporting information, p. 1533 - 1550 (2013/10/22)
Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment corresponding to C1-C9 has been synthesized in high yield and demonstrated to be a competent substrate for the nickel(0)-catalyzed coupling with a model epoxide. Several synthetic approaches toward the C10-C26 epoxide have been pursued. The C13 stereocenter can be set by allylation and reductive decyanation of a cyanohydrin acetonide. A mild, fluoride-promoted decarboxylation enables construction of the C15-C16 bond by an aldol reaction. The product of this transformation is of the correct oxidation state and potentially three steps removed from the targeted epoxide fragment.
Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
Dieckmann, Michael,Menche, Dirk
supporting information, p. 228 - 231 (2013/03/28)
A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydrox
Iodocyclization and prins-type macrocyclization: An efficient formal synthesis of leucascandrolide A
Yadav,Pattanayak, Manas R.,Das, Pragna P.,Mohapatra, Debendra K.
supporting information; experimental part, p. 1710 - 1713 (2011/06/17)
The formal total synthesis of leucascandrolide A has been achieved in 20 steps from a known epoxide with an overall yield of 11.5% following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4- dihydropyrans and a Lewis acid
Short diastereoselective synthesis of the C1-C13 (AB Spiroacetal) and C17-C28 fragments (CD spiroacetal) of spongistatin 1 and 2 through double chain-elongation reactions
Flowers, Christopher L.,Vogel, Pierre
supporting information; experimental part, p. 14074 - 14082 (2011/02/23)
A unique and practical synthetic sequence for rapid access to polyketides and to further the spiroacetals derived from them, which utilizes a bidirectional Hosomi-Sakurai allylation approach around key allylsilanes in the synthesis of the AB and CD ring s
Asymmetric total synthesis of rugulactone, an α-pyrone from Cryptocarya rugulosa
Allais, Florent,Aouhansou, Mahoulo,Majira, Amel,Ducrot, Paul-Henri
experimental part, p. 2787 - 2793 (2010/10/18)
A total asymmetric synthesis of rugulactone, a naturally occuring -pyrone isolated from Cryptocarya rugulosa, is reported. The synthesis involved a cross-metathesis coupling reaction to construct the internal E-olefin group, a Still-Gennari olefination to
