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Masaya Nakata

Bio: Masaya Nakata is an academic researcher from Keio University. The author has contributed to research in topics: Total synthesis & Diene. The author has an hindex of 31, co-authored 214 publications receiving 2873 citations. Previous affiliations of Masaya Nakata include Mitsubishi Tanabe Pharma & Harvard University.
Topics: Total synthesis, Diene, Dithiane, Enediyne, Aryl


Papers
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Journal ArticleDOI
TL;DR: In this paper, a fully protected palytoxin carboxylic acid was synthesized from eight building blocks using Ni(II)/Cr(II)-mediated coupling reaction.
Abstract: The total synthesis of a fully protected palytoxin carboxylic acid was achieved from eight building blocks. The C.22-C.23 and C.37-C.38 bonds were formed via Wittig olefination, followed by hydrogenation. The Ni(II)/Cr(II)-mediated coupling reaction was utilized for formation of the C.7-C.8 annd C.84-C.85 bonds. The TIOH-accelerated diene synthesis was applied for formation of the C.75-C.76 bond. The C.98-C.99 olefinic bond was introduced by a Wittig reaction, whereas the C.51-C.52 olefinic bond was introduced by a Horner-Emmons reaction, followed by stereoselective LiBH 4 /EuCl 3 reduction

108 citations

Journal ArticleDOI
27 May 2004-Nature
TL;DR: In this article, the colorless, viscous sweat of the hippopotamus gradually turns red, and then brown as the pigment polymerizes, and the unstable red and orange pigments turn out to be non-benzenoid aromatic compounds that are unexpectedly acidic and have antibiotic and sunscreen activity.
Abstract: Within a few minutes of perspiration, the colourless, viscous sweat of the hippopotamus gradually turns red, and then brown as the pigment polymerizes. Here we isolate and characterize the pigments responsible for this colour reaction. The unstable red and orange pigments turn out to be non-benzenoid aromatic compounds that are unexpectedly acidic and have antibiotic as well as sunscreen activity.

71 citations

Journal ArticleDOI
TL;DR: The highly stereoselective total synthesis of the macrolide antibiotic, bafilomycin A(1) (1), the first specific potent inhibitor of vacuolar H(+)-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 16-membered tetraenic lactone and beta-hydroxyl hemiacetal side-chain subunits.
Abstract: The highly stereoselective total synthesis of the macrolide antibiotic, bafilomycin A1 (1), the first specific potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 16-membered tetraenic lactone and β-hydroxyl hemiacetal side-chain subunits. The C1−C17 16-membered lactone aldehyde 2 was synthesized through the coupling of the C5−C11 vinyl iodide 4 and the C12−C17 vinylstannane 5, followed by construction of the C1−C4 diene and macrolactonization. The aldol coupling of 2 and the C18−C25 ethyl ketone 3 followed by desilylation provided 1, which was identical with natural bafilomycin A1. The key synthetic segments 3−5 were effectively synthesized from the readily available chiral materials, d-glucose, ethyl (S)-lactate, and methyl (S)-3-hydroxy-2-methylpropionate, respectively.

67 citations

Journal ArticleDOI
TL;DR: It is found that polymerization of the compound at high concentrations via ene reaction abolishes its toxicity, a new type of mushroom poisoning that is indicated by an increase in serum creatine phosphokinase activity in mice.
Abstract: We have isolated the small, highly strained carboxylic acid cycloprop-2-ene carboxylic acid from the Asian toxic mushroom Russula subnigricans. This compound is responsible for fatal rhabdomyolysis, a new type of mushroom poisoning that is indicated by an increase in serum creatine phosphokinase activity in mice. We found that polymerization of the compound at high concentrations via ene reaction abolishes its toxicity.

64 citations

Journal ArticleDOI
TL;DR: O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone under neutral conditions proceeds smoothly to give the corresponding 2, 3-unsaturated glycosides in high yields.
Abstract: O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under neutral conditions proceeds smoothly to give the corresponding 2,3-unsaturated glycosides in high yields.

63 citations


Cited by
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Journal ArticleDOI
TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.

4,649 citations

Journal ArticleDOI
29 Nov 1991-Science
TL;DR: The ability to prepare structures in the upper part of this range of sizes would open a route to structures comparable in size (and perhaps complementary in function) to those that can be prepared by microlithography and other techniques of microfabrication.
Abstract: Molecular self-assembly is the spontaneous association of molecules under equilibrium conditions into stable, structurally well-defined aggregates joined by noncovalent bonds. Molecular self-assembly is ubiquitous in biological systems and underlies the formation of a wide variety of complex biological structures. Understanding self-assembly and the associated noncovalent interactions that connect complementary interacting molecular surfaces in biological aggregates is a central concern in structural biochemistry. Self-assembly is also emerging as a new strategy in chemical synthesis, with the potential of generating nonbiological structures with dimensions of 1 to 10(2) nanometers (with molecular weights of 10(4) to 10(10) daltons). Structures in the upper part of this range of sizes are presently inaccessible through chemical synthesis, and the ability to prepare them would open a route to structures comparable in size (and perhaps complementary in function) to those that can be prepared by microlithography and other techniques of microfabrication.

3,119 citations

01 Dec 1991
TL;DR: In this article, self-assembly is defined as the spontaneous association of molecules under equilibrium conditions into stable, structurally well-defined aggregates joined by noncovalent bonds.
Abstract: Molecular self-assembly is the spontaneous association of molecules under equilibrium conditions into stable, structurally well-defined aggregates joined by noncovalent bonds. Molecular self-assembly is ubiquitous in biological systems and underlies the formation of a wide variety of complex biological structures. Understanding self-assembly and the associated noncovalent interactions that connect complementary interacting molecular surfaces in biological aggregates is a central concern in structural biochemistry. Self-assembly is also emerging as a new strategy in chemical synthesis, with the potential of generating nonbiological structures with dimensions of 1 to 10(2) nanometers (with molecular weights of 10(4) to 10(10) daltons). Structures in the upper part of this range of sizes are presently inaccessible through chemical synthesis, and the ability to prepare them would open a route to structures comparable in size (and perhaps complementary in function) to those that can be prepared by microlithography and other techniques of microfabrication.

2,591 citations

Journal ArticleDOI
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Abstract: In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

2,268 citations

Journal ArticleDOI
Chao-Jun Li1
TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
Abstract: 4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

2,031 citations