Total synthesis of the aglycone of IB-00208

Knueppel, Daniel; Yang, Jingxian; Cheng, Bo; Mans, Douglas M.; Martin, Stephen F.

doi:10.1016/j.tet.2015.05.024

Cited by 24 publications

(21 citation statements)

References 55 publications

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“…[3] FD-594 differs from other polycyclic xanthones such as kigamicin A (3) [4] and kibdelone C (4) [5] primarily in oxidation state and functional groups on the C and F rings. The intriguing structures and biological activities of polycyclic xanthones have led many groups to develop syntheses, [1] including the Kelly, [6] Porco, [7] Ready, [8] and Martin [9] groups. A breakthrough toward the synthesis of FD-594 came in 2009, when Suzuki and co-workers prepared the corresponding aglycone.…”

Section: Asymmetric Total Synthesis Of the Complex Polycyclic Xanthonmentioning

confidence: 99%

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

et al. 2020

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A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD‐594, a complex polycyclic xanthone natural product from Streptomyces sp. TA‐0256, in a longest linear sequence (LLS) of 20 steps. The trans‐9,10‐dihydrophenanthrene‐9,10‐diol fragment (B‐C‐D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu‐mediated oxidative cyclization. Late‐stage stereoselective glycosylation assembled the angular hexacyclic framework with a β‐linked 2,6‐dideoxy trisaccharide fragment.

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Section: Asymmetric Total Synthesis Of the Complex Polycyclic Xanthonmentioning

confidence: 99%

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

et al. 2020

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“…After quantification, the DNA samples of 574 plants (190 [12], we filtered by missing allele and chromosome. Then, we computed the SNP and genotype call rates and the minor allele 6 frequency (MAF), employing the R package HapEstXXR [13]. After filtering by MAF > 0.01, we imputed based on Beagle [14], using the R package synbreed [15].…”

Section: Dna Extraction Genotyping-by-sequencing (Gbs) Snp Callingmentioning

confidence: 99%

Linkage disequilibrium and haplotype block patterns in popcorn populations

Andrade

Viana

Pereira

et al. 2019

Preprint

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Linkage disequilibrium (LD) analysis provides information on evolutionary aspects of the 9 populations and allows selecting populations and single nucleotide polymorphisms (SNPs) for 10 association studies. Recently, haplotype blocks have been used to increase the power of quantitative 11 trait loci detection in genome-wide association studies and the prediction accuracy with genomic 12 selection. The objectives of this study were to compare the degree of LD, the LD decay, the LD 13 decay extent, and the number and length of haplotype blocks in the populations and to elaborate the 14 first LD map for maize, for elucidating if the maize chromosomes also had a pattern of interspaced 15 regions of high and low rates of recombination. We used a biparental temperate population, a 16 tropical synthetic, and a tropical breeding population, genotyped for approximately 75,000 SNPs. 17The level of LD expressed by the r 2 values is surprisingly low (0.02, 0.04, and 0.04), but 18 comparable to some non-isolated human populations. The general evidence is that the synthetic is 19 the population with higher LD. It is not expected a significant advantage of haplotype-based 20 association study and along generations genomic selection due to the reduced number of SNPs in 21 the haplotype blocks (2 to 3). The results concerning LD decay (rapid decay after 5-10 kb) and LD 22 decay extent (along up to 300 kb) are in the range observed with maize inbred line panels. Our most 23 important result is that maize chromosomes had a pattern of regions of extensive LD interspaced 24 with regions of low LD. However, our simple simulated LD map provides evidence that this pattern 25 can reflect regions with differences of allele frequencies and LD level (expressed by D') and not 26 regions with high and low rates of recombination. 27 Keywords: gametic phase disequilibrium; LD map; haplotype blocks; intragenic LD. Introduction Linkage disequilibrium (LD) analysis is important to humans, other animal species, and plants because the results can be used for positional cloning, provide information on rate of recombination, gene conversion, and evolutionary aspects of the populations, including recombination history, mutation, selection, genetic drift, and admixture, and allows selecting populations and single nucleotide polymorphisms (SNPs) for association studies [1]. The most common LD measures are D' and r 2 . The statistic D' is the ratio between D (the difference between products of haplotypes, D = P(AB).P(ab)  P(Ab).P(aB)) and the deviation of the actual gametic frequency from linkage equilibrium [2]. The statistic r 2 is the square of the correlation between the values of alleles at two loci in the same gamete, where D is the covariance [3]. Additional information on historical recombination is provided by the analysis of the haplotype blocks pattern in populations. A haplotype block is a chromosome region in which there are few haplotypes (combinations of alleles of multiple SNPs within a haplotype block) (2-4 per block), and for which the ...

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“…Such compounds range in structural complexity from the tricyclic tetramethoxyxanthone 43 to the polycyclic representatives IB-00208, 44 citreamicin η, 45 and kibdelone C (Figure 5, xanthone rings highlighted in blue). Many compounds of this class exhibit potent antibacterial and anticancer activity.…”

Section: General Route To Polycyclic Xanthone Natural Productsmentioning

confidence: 99%

“…44 Because both enantiomers of propylene oxide are commercially available, we would be able to introduce the correct stereochemistry at C3 once the absolute configuration in IB-00208 was known. After removal of the two O -methyl groups from 121 , acid-catalyzed cyclization furnished 122 , which was converted via a Duff formylation, followed by protection and Wittig olefination to give 123 .…”

Section: General Route To Polycyclic Xanthone Natural Productsmentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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Diverse structural types of natural products and their mimics have served as targets of opportunity in our laboratory to inspire the discovery and development of new methods and strategies to assemble polyfunctional and polycyclic molecular architectures. Furthermore, our efforts toward identifying novel compounds having useful biological properties led to the creation of new targets, many of which posed synthetic challenges that required the invention of new methodology. In this Perspective, selected examples of how we have exploited a diverse range of natural products and their mimics to create, explore, and solve a variety of problems in chemistry and biology will be discussed. The journey was not without its twists and turns, but the unexpected often led to new revelations and insights. Indeed, in our recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding.

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Total synthesis of the aglycone of IB-00208

Cited by 24 publications

References 55 publications

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

Linkage disequilibrium and haplotype block patterns in popcorn populations

Natural Products and Their Mimics as Targets of Opportunity for Discovery

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