6512-27-2Relevant academic research and scientific papers
Synthesis process of natural product Agrimonolide (I) racemate extracted from agrimonia pilosa
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Paragraph 0012; 0013; 0014, (2018/12/05)
The invention belongs to the field of chemical synthesis, and particularly relates to a total synthesis method of a natural product 6,8-dyhydroxyl-3-(4'-methoxyphenyl ethyl) isochroman-1-ketone (dl-Agrimonolide (I)) extracted from a plant agrimonia pilosa
Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A9, and (±)-Fasamycin A: Structure-Activity Relationship Studies against Drug-Resistant Bacteria
Huang, Jing-Kai,Yang Lauderdale, Tsai-Ling,Lin, Chun-Cheng,Shia, Kak-Shan
, p. 6508 - 6523 (2018/05/30)
Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (±)-naphthacemycin A9, and (±)-fasamycin A in a highly convergent and pra
Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation
Nicolaou,Hale, Christopher R. H.,Nilewski, Christian,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Nilewski, Lizanne G.,Beabout, Kathryn,Wang, Tim T.,Shamoo, Yousif
, p. 12137 - 12160 (2014/11/08)
The details of the total synthesis of viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.
Total synthesis and structural revision of viridicatumtoxin B
Nicolaou,Nilewski, Christian,Hale, Christopher R. H.,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Koch, Lizanne G.
supporting information, p. 8736 - 8741 (2013/09/12)
Will the real viridicatumtoxin B please stand up: The total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline-like antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule. Copyright
Targeting the Hsp90 chaperone: Synthesis of novel resorcylic acid macrolactone inhibitors of Hsp90
Day, James E. H.,Sharp, Swee Y.,Rowlands, Martin G.,Aherne, Wynne,Workman, Paul,Moody, Christopher J.
supporting information; experimental part, p. 2758 - 2763 (2010/07/04)
A series of benzo-macrolactones has been prepared by chemical synthesis, and evaluated as inhibitors of heat shock protein 90 (Hsp90), an emerging attractive target for novel cancer therapeutic agents. A new synthesis of these resorcylic acid macrolactone analogues of the natural product radicicol is described in which the key steps are the acylation and ring opening of a homophthalic anhydride to give an isocoumarin, followed by a ring-closing metathesis to form the macrocycle. The methodology has been extended to a novel series of macrolactones incorporating a 1,2,3-triazole ring.
An improved synthesis of resorcylic acid macrolactone inhibitors of Hsp90
Day, James E. H.,Blake, Alexander J.,Moody, Christopher J.
scheme or table, p. 1567 - 1570 (2009/11/30)
A synthesis of resorcylic acid macrolactone analogues of the natural product radicicol is described in which the key steps are the acylation and ring opening of a homophthalic anhydride to give an isocoumarin, followed by a ring-closing metathesis to form
Formal synthesis of angiogenesis inhibitor NM-3
Bauta, William E.,Lovett, Dennis P.,Cantrell Jr., William R.,Burke, Brian D.
, p. 5967 - 5973 (2007/10/03)
We report the formal synthesis of angiogenesis inhibitor NM-3 (1) in six steps from either of the 2,4-dimethoxyhalobenzenes 13a,b or 3,5-dimethoxychlorobenzene (13c). The first key reaction is the regiospecific alkylation/rearrangement between the aryne derived from 13a-c with sodium diethylmalonate in THF to produce diester 11, which after hydrolysis and cyclization affords homophthalic anhydride 3. The second is the reaction of anhydride 3 with either ethyl 2-methylmalonate (28a), in the presence of 1,1′-carbonyldiimidazole, or ethyl-2-methylmalonyl chloride (28b) under basic conditions to afford key isocoumarin 27. The conversion of 27 constitutes a formal synthesis of NM-3.
Synthesis and cytotoxic activity of tetracenomycin d and of saintopin analogues
Martin, Philippe,Rodier, Stephane,Mondon, Martine,Renoux, Brigitte,Pfeiffer, Bruno,Renard, Pierre,Pierre, Alain,Gesson, Jean-Pierre
, p. 253 - 260 (2007/10/03)
Regiospecific synthesis of title compounds is based either on cycloaddition of ketene acetals derived from Hagemann's ester or of homophthalic anhydrides. Thus, tetracenomycin D and 3,8-di-O-methyl saintopin have been prepared in few steps. New derivatives of 10-deoxysaintorpin have been also obtained. Evaluation of their cytotoxicity against L1210 leukemia cells are reported. Copyright
