3686-57-5Relevant academic research and scientific papers
First total synthesis of kipukasin A
Li, Chuang,Ding, Haixin,Ruan, Zhizhong,Zhou, Yirong,Xiao, Qiang
, p. 855 - 862 (2017)
In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-is
Production of New Cladosporin Analogues by Reconstitution of the Polyketide Synthases Responsible for the Biosynthesis of this Antimalarial Agent
Cochrane, Rachel V. K.,Sanichar, Randy,Lambkin, Gareth R.,Reiz, Bla,Xu, Wei,Tang, Yi,Vederas, John C.
, p. 664 - 668 (2016)
The antimalarial agent cladosporin is a nanomolar inhibitor of the Plasmodium falciparum lysyl-tRNA synthetase, and exhibits activity against both blood- and liver-stage infection. Cladosporin can be isolated from the fungus Cladosporium cladosporioides, where it is biosynthesized by a highly reducing (HR) and a non-reducing (NR) iterative type I polyketide synthase (PKS) pair. Genome sequencing of the host organism and subsequent heterologous expression of these enzymes in Saccharomyces cerevisiae produced cladosporin, confirming the identity of the putative gene cluster. Incorporation of a pentaketide intermediate analogue indicated a 5+3 assembly by the HR PKS Cla2 and the NR PKS Cla3 during cladosporin biosynthesis. Advanced-intermediate analogues were synthesized and incorporated by Cla3 to furnish new cladosporin analogues. A putative lysyl-tRNA synthetase resistance gene was identified in the cladosporin gene cluster. Analysis of the active site emphasizes key structural features thought to be important in resistance to cladosporin.
Efficient total synthesis of (S)-dihydroresorcylide, a bioactive twelve-membered macrolide
Zhang, Li,Ma, Wenquan,Xu, Lili,Deng, Fei,Guo, Yuewei
, p. 339 - 343 (2013/08/22)
The efficient synthesis of (S)-dihydroresorcylide (1a) along with trans-resorcylide dimethyl ether (2b), was achieved in linear 9 steps from commercially available orcinol monohydrate (6) with esterification, carbonylation, and ring-closing metathesis (RCM) as the key steps in the synthetic sequence. Copyright
MACROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF KINASES AND HSP90
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Page/Page column 92; 166, (2010/11/30)
Disclosed are macrocyclic compounds of formulae I-V,which are analogs of the pochonin resorcylic acid lactones, and processes for the preparation of the compounds. The compounds disclosed are useful as inhibitors of kinases and Heat Shock Protein 90 (HSP 90). Also disclosed are pharmaceutical compositions comprising an effective kinase-inhibiting amount or an effective HSP90-inhibiting amount of the compounds and methods for the treatment of disorders that are mediated by kinases and HSP90.
COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA
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Page/Page column 49; 59-60, (2008/06/13)
There is described compounds for use in therapy, said compounds being defined by Formula (1): There is also described an anti-proliferative composition comprising one or more compounds according to Formula (1), and a method of treatment of neoplasia comprising the administration of such a compound or composition.
Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities
Wang, Ping,Zhang, Zhaojun,Yu, Biao
, p. 8884 - 8889 (2007/10/03)
CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinol p-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approac
An anionic polycondensation strategy for the synthesis of dibenzoxanthenones: Progress toward the synthesis of hypoxyxylerone
Chevenier, Emmanuel,Lucatelli, Christophe,Pandya, Urvish,Wang, Wei,Gimbert, Yves,Greene, Andrew E.
, p. 2693 - 2696 (2007/10/03)
An anionic polycondensation has been used as the key step in a highly convergent strategy for the preparation of hypoxyxylerone derivatives.
Process for the manufacture of hypoxyxylerone derivatives
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, (2008/06/13)
The present invention relates to the total synthesis of hypoxyxylerone derivatives (formula I) and their biological activities. R1-R5 are as described in the description.
Total synthesis of (S)-(+)-citreofuran by ring closing alkyne metathesis
Fuerstner, Alois,Castanet, Anne-Sophie,Radkowski, Karin,Lehmann, Christian W.
, p. 1521 - 1528 (2007/10/03)
A concise total synthesis of citreofuran 4 is described, a structurally unique octaketide derivative belonging to the curvularin family. Key steps involve the elaboration of orsellinic acid methyl ester 5 to acid 14, which converts, on attempted formation of the corresponding acid chloride, to the 3-alkoxyisocoumarin derivative 20. This heterocycle can be used as an activated ester to give ketone 21 on treatment with 3-pentynylmagnesium bromide in the presence of TMSCl as the activating agent. Ring-closing alkyne metathesis (RCAM) of diyne 21 catalyzed by (tBuO)3W≡CCMe3 affords the strained cycloalkyne 22. Treatment with acid renders its triple bond susceptible to nucleophilic attack by the adjacent carbonyl group, thus leading to a transannular cycloaromatization with formation of the intact skeleton of citreofuran. An X-ray crystallographic study reveals conformational details about this natural product. Finally, it is shown that 4 as well as its protected precursor 23 are able to cleave double-stranded DNA under oxidative conditions.
Total syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands
Furstner,Thiel,Kindler,Bartkowska
, p. 7990 - 7995 (2007/10/03)
Total syntheses of the bioactive orsellinic acid derivatives zearalenone 3 and lasiodiplodin 1 are reported based on a ring-closing metathesis (RCM) reaction of styrene precursors as the key steps. These and closely related macrocyclizations are catalyzed
