Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/the-total-synthesis-of-heraclemycin-b-through-ketosulfoxide-and-Z71J1WHbMn
References (42)
-
P. Pfeffer, L. Silbert, John Chirinko (1972)
.alpha. Anions of carboxylic acids. II. Formation and alkylation of .alpha.-metalated aliphatic acidsJournal of Organic Chemistry, 37
-
B. O'Keefe, Douglas Mans, David Kaelin, Stephen Martin (2010)
Total synthesis of isokidamycin.Journal of the American Chemical Society, 132 44
-
L. Tietze, K. Gericke, I. Schuberth (2007)
Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor ActivityEuropean Journal of Organic Chemistry, 2007
-
M. Hansen, Sanghyeon Yun, L. Hurley (1995)
Hedamycin intercalates the DNA helix and, through carbohydrate-mediated recognition in the minor groove, directs N7-alkylation of guanine in the major groove in a sequence-specific manner.Chemistry & biology, 2 4
-
Miaomiao Liu, Wael Abdel-Mageed, B. Ren, Wenni He, Pei Huang, Xiaolin Li, K. Bolla, Hui Guo, Caixia Chen, Fuhang Song, Huanqin Dai, R. Quinn, T. Grkovic, Xiao-ping Zhang, Xueting Liu, Lixin Zhang (2013)
Endophytic Streptomyces sp. Y3111 from traditional Chinese medicine produced antitubercular pluramycinsApplied Microbiology and Biotechnology, 98
-
N. Kanda (1971)
A new antitumor antibiotic, kidamycin. I. Isolation, purification and properties of kidamycin.The Journal of antibiotics, 24 9
-
P. Javidpour, Abhirup Das, C. Khosla, S. Tsai (2011)
Structural and biochemical studies of the hedamycin type II polyketide ketoreductase (HedKR): molecular basis of stereo- and regiospecificities.Biochemistry, 50 34
-
L. Tu, T. Melendy, T. Beerman (2004)
DNA damage responses triggered by a highly cytotoxic monofunctional DNA alkylator, hedamycin, a pluramycin antitumor antibiotic.Molecular cancer therapeutics, 3 5
-
Benjamin Wright, J. Hartung, F. Peng, R. Water, Haibo Liu, Quen-Hui Tan, T. Chou, S. Danishefsky (2008)
Synthesis of pluraflavin A "aglycone".Journal of the American Chemical Society, 130 49
-
K. Krohn, J. Vitz (2004)
Total Synthesis of Premithramycinone H and Related Anthrapyran AntibioticsEuropean Journal of Organic Chemistry, 2004
-
H. Uno, K. Sakamoto, E. Honda, N. Ono (1999)
Total synthesis of (S)-espicufolin and absolute structure determinaton of espicufolinChemical Communications
-
Laura Foulgoc, D. Sissouma, M. Evain, Sylvain Collet, A. Guingant (2012)
A Diels-Alder Approach to Anthrapyran AntibioticsSynlett, 23
-
M. Strandtmann, S. Klutchko, Marvin Cohen, J. Shavel (1972)
Heterocyclic syntheses with β‐ketosulfoxides. I. New syntheses of chromones, flavones, thioindigo and thioflavonesJournal of Heterocyclic Chemistry, 9
-
S. Pestka, A. Nakagawa, S. Ōmura (1974)
Effect of Leucomycins and Analogues on Binding [14C]Erythromycin to Escherichia coli RibosomesAntimicrobial Agents and Chemotherapy, 6
-
L. Tietze, Ramakrishna Singidi, K. Gericke (2006)
First enantioselective total synthesis and structure determination of the anthrapyran metabolite gamma-indomycinone.Organic letters, 8 25
-
Zhongbo Fei, F. McDonald (2005)
Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.Organic letters, 7 17
-
L. Tietze, K. Gericke, Ramakrishna Singidi, I. Schuberth (2007)
Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin.Organic & biomolecular chemistry, 5 8
-
K. Krohn, Hoan Tran-Thien, Ishtiaq Ahmed (2011)
General Approach to Anthrapyran Antibiotics Exemplified by the Synthesis of rac-γ-IndomycinoneEuropean Journal of Organic Chemistry, 2011
-
D. Hsu, Takashi Matsumoto, Keisuke Suzuki (2006)
Concise Synthesis of (±)-γ-IndomycinoneChemistry Letters, 35
-
A. Prakash, A. Moore, V. Murray, C. Matías, W. Mcfadyen, G. Wickham (1995)
Comparison of the sequence selectivity of the DNA-alkylating pluramycin antitumour antibiotics DC92-B and hedamycin.Chemico-biological interactions, 95 1-2
-
D. Dess, J. Martin (1991)
A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 speciesJournal of the American Chemical Society, 113
-
C. Snyder, H. Rapoport (1972)
Oxidative cleavage of hydroquinone ethers with argentic oxideJournal of the American Chemical Society, 94
-
P. Gramatica, M. Gianotti, G. Speranza, P. Manitto (1986)
Synthesis of naturally occurring 2,5-dialkylchromones. I: Synthesis of aloesone and aloesolHeterocycles, 24
-
Y. Lee, A. Morehead (1995)
A new route for the synthesis of furanoflavone and furanochalcone natural productsTetrahedron, 51
-
L. Parfenova, T. Berestova, T. Tyumkina, P. Kovyazin, L. Khalilov, R. Whitby, U. Dzhemilev (2010)
Enantioselectivity of chiral zirconocenes as catalysts in alkene hydro-, carbo- and cycloalumination reactionsTetrahedron-asymmetry, 21
-
K. Kitamura, Y. Ando, Takashi Matsumoto, Keisuke Suzuki (2014)
Synthesis of the pluramycins 1: two designed anthrones as enabling platforms for flexible bis-C-glycosylation.Angewandte Chemie, 53 5
-
L. Tietze, K. Gericke, Ramakrishna Singidi (2006)
Enantioselektive Totalsynthese und Strukturaufklärung des antiherpetischen Anthrapyran-Antibiotikums AH-1763 IIa†Angewandte Chemie, 118
-
Jacques Savard, P. Brassard (1984)
Reactions of ketene acetals-14 The use of simple mixed vinylketene acetals in the annulation of quinonesTetrahedron, 40
-
L. Tietze, Ramakrishna Singidi, K. Gericke (2007)
Total Synthesis of the Proposed Structure of the Anthrapyran Metabolite δ‐IndomycinoneChemistry: A European Journal, 13
-
J. Augustine, Y. Naik, Subba Poojari, Nagaraja Chowdappa, B. Sherigara, Kummara Areppa (2009)
gem-DibromomethylAromatics: Efficient Aldehyde Equivalents in the Knoevenagel-DoebnerReactionSynthesis, 2009
-
J. Lanier, J. Whitcher, C. Dawson, Jang Oh (1974)
Proflavine and Light in the Treatment of Experimental Herpetic Ocular InfectionsAntimicrobial Agents and Chemotherapy, 6
-
M. Kozlowski, Elizabeth Dugan, E. Divirgilio, Katja Maksimenka, G. Bringmann (2007)
Asymmetric Total Synthesis of Nigerone and ent‐Nigerone: Enantioselective Oxidative Biaryl Coupling of Highly Hindered NaphtholsAdvanced Synthesis & Catalysis, 349
-
James Rixson, James Abraham, Yuki Egoshi, B. Skelton, K. Young, J. Gilbert, J. Sakoff, K. Gericke, A. McCluskey, S. Stewart (2015)
The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans.Bioorganic & medicinal chemistry, 23 13
-
L. Tietze, K. Gericke, Ramakrishna Singidi (2006)
Enantioselective total synthesis and structure determination of the antiherpetic anthrapyran antibiotic AH-1763 IIa.Angewandte Chemie, 45 42
-
Naama Hen, M. Bialer, B. Wlodarczyk, R. Finnell, B. Yagen (2010)
Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide.Journal of medicinal chemistry, 53 10
-
N. Kanda, M. Kono, K. Asano (1972)
A new antitumor antibiotic, kidamycin. II. Experimental treatment of cancer with kidamycin.The Journal of antibiotics, 25 10
-
James Rixson, B. Skelton, George Koutsantonis, K. Gericke, S. Stewart (2013)
Domino reactions for the synthesis of anthrapyran-2-ones and the total synthesis of the natural product (±)-BE-26554A.Organic letters, 15 18
-
Rishikesh Narayan, A. Antonchick (2014)
Hypervalent iodine-mediated selective oxidative functionalization of (thio)chromones with alkanes.Chemistry, 20 16
-
Xuesong Wang, Guolin Cheng, Xiuling Cui (2014)
Tandem synthesis of 3-allyl-chromones from alkynones and allylic alcohols under metal-free conditions.Chemical communications, 50 6
-
J. Augustine, Y. Naik, A. Mandal, Nagaraja Chowdappa, Vinuthan Praveen (2007)
gem-Dibromomethylarenes: A Convenient Substitute for Noncommercial Aldehydes in the Knoevenagel−Doebner Reaction for the Synthesis of α,β-Unsaturated Carboxylic AcidsJournal of Organic Chemistry, 72
-
D. Hodgson, C. Bray, N. Kindon (2004)
Enamines from terminal epoxides and hindered lithium amides.Journal of the American Chemical Society, 126 22
-
F. Hauser, R. Rhee (1979)
4H-Anthra[1,2-b]pyran antibiotics. Total synthesis of the methyl ether of kidamycinoneJournal of the American Chemical Society, 101
- Publisher
- Wiley
- Copyright
- © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201500184
- Publisher site
- See Article on Publisher Site
Abstract
Herein we describe a total synthesis of the natural product heraclemycin B. This synthetic approach follows a Diels–Alder strategy to form the anthracenone core followed by a β‐ketosulfoxide and aldehyde annulation to form the 4‐pyranone D ring. The spectral data for the synthesized product matches that reported in the isolation studies.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Sep 1, 2015
Keywords: ; ; ; ;