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Marinomycin

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https://www.readbyqxmd.com/read/24962551/total-synthesis-of-marinomycin-a-based-on-a-direct-dimerization-strategy
#1
Tatsuya Nishimaru, Masashi Kondo, Kimito Takeshita, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama
The asymmetric total synthesis of (+)-marinomycin A, a 44-membered macrodiolide antitumor agent and antibiotic isolated from a marine actinomycete, Marinispora strain CNQ-140, is reported. The key features of the synthesis include the highly convergent stereocontrolled construction of the monomeric hydroxy salicylate starting from asymmetric epoxidation of the σ-symmetrical dialkenyl carbinol, and an unprecedented direct dimerization through NaHMDS-promoted double transesterification.
August 4, 2014: Angewandte Chemie
https://www.readbyqxmd.com/read/22824902/total-synthesis-of-marinomycin-a-using-salicylate-as-a-molecular-switch-to-mediate-dimerization
#2
P Andrew Evans, Mu-Hua Huang, Michael J Lawler, Sergio Maroto
Antibiotics play a significant role in human health because of their ability to treat life-threatening bacterial infections. The growing problems with antibiotic resistance have made the development of new antibiotics a World Health Organization priority. Marinomycin A is a member of a new class of bis-salicylate-containing polyene macrodiolides, which have potent antibiotic activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium. Herein, we describe a triply convergent synthesis of this agent using the salicylate as a novel molecular switch for the chemoselective construction of the macrodiolide...
August 2012: Nature Chemistry
https://www.readbyqxmd.com/read/19769335/synthesis-of-the-monomeric-counterpart-of-marinomycin-a
#3
Dominique Amans, Laurianne Bareille, Véronique Bellosta, Janine Cossy
An efficient and highly convergent synthesis of the monomeric counterpart of the antitumor-antibiotic marine natural product marinomycin A was achieved by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the (E)-configured C20-C21 double bond, and a Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed Stille cross-coupling to construct the tetraene moiety.
October 16, 2009: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/17355145/an-efficient-and-stereoselective-synthesis-of-the-monomeric-counterpart-of-marinomycin-a
#4
Dominique Amans, Véronique Bellosta, Janine Cossy
[structure: see text] The monomeric counterpart of marinomycin A, an antitumor-antibiotic marine natural product, was synthesized efficiently in 11 steps from the commercially available ethyl (R)-(-)-3-hydroxybutyrate. The strategy was highlighted by a crucial regio- and stereoselective cross-metathesis to form the C20-C21 double bond, enantioselective allyltitanations to control the configuration of the C17, C23, and C25 stereogenic centers, and a stereocontrolled construction of the tetraene moiety based on an original Horner-Wadsworth-Emmons olefination followed by a Pd-catalyzed cross-coupling...
April 12, 2007: Organic Letters
https://www.readbyqxmd.com/read/17249678/total-synthesis-of-marinomycins-a-c-and-of-their-monomeric-counterparts-monomarinomycin-a-and-iso-monomarinomycin-a
#5
K C Nicolaou, Andrea L Nold, Robert R Milburn, Corinna S Schindler, Kevin P Cole, Junichiro Yamaguchi
Marinomycins A-C (1-3), and their monomeric analogues monomarinomycin A (m-1) and iso-monomarinomycin A (m-2), were synthesized by a convergent strategy from key building blocks ketophosphonate 5, aldehyde 6, and dienyl bromide carboxylic acid 7. The first attempt to construct marinomycin A [1, convertible to marinomycins B (2) and C (3) by light] by direct Suzuki-type dimerization/cyclization of boronic acid dienyl bromide 4 led to premature ring closure to afford, after global desilylation, monomarinomycin A (m-1) and iso-monomarinomycin A (m-2) in good yield and only small amounts (< or =2%) of the desired product...
February 14, 2007: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/16977657/total-synthesis-of-marinomycins-a-c
#6
K C Nicolaou, Andrea L Nold, Robert R Milburn, Corinna S Schindler
No abstract text is available yet for this article.
October 6, 2006: Angewandte Chemie
https://www.readbyqxmd.com/read/16448135/marinomycins-a-d-antitumor-antibiotics-of-a-new-structure-class-from-a-marine-actinomycete-of-the-recently-discovered-genus-marinispora
#7
Hak Cheol Kwon, Christopher A Kauffman, Paul R Jensen, William Fenical
Four antitumor-antibiotics of a new structure class, the marinomycins A-D (1-4), were isolated from the saline culture of a new group of marine actinomycetes, for which we have proposed the name "Marinispora". The structures of the marinomycins, which are unusual macrodiolides composed of dimeric 2-hydroxy-6-alkenyl-benzoic acid lactones with conjugated tetraene-pentahydroxy polyketide chains, were assigned by combined spectral and chemical methods. In room light, marinomycin A slowly isomerizes to its geometrical isomers marinomycins B and C...
February 8, 2006: Journal of the American Chemical Society
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