The Experts below are selected from a list of 975 Experts worldwide ranked by ideXlab platform
Thomas E. Prisinzano - One of the best experts on this subject based on the ideXlab platform.
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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.
The Journal of Organic Chemistry, 2018Co-Authors: Alexander M. Sherwood, Samuel E. Williamson, Stephanie N. Johnson, Anil Yilmaz, Victor W. Day, Thomas E. PrisinzanoAbstract:A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (−)-aspinolide A and (−)-5-epi-aspinolide A utilizing a catalytic Nozaki–Hiyama–Kishi Reaction to close the macrolide in the final step in 65–84% yields.
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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)‑4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
2017Co-Authors: Alexander M. Sherwood, Samuel E. Williamson, Stephanie N. Johnson, Anil Yilmaz, Victor W. Day, Thomas E. PrisinzanoAbstract:A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (−)-aspinolide A and (−)-5-epi-aspinolide A utilizing a catalytic Nozaki–Hiyama–Kishi Reaction to close the macrolide in the final step in 65–84% yields
Boris M Seletsky - One of the best experts on this subject based on the ideXlab platform.
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from micrograms to grams scale up synthesis of eribulin mesylate
Natural Product Reports, 2013Co-Authors: Wanjun Zheng, Boris M SeletskyAbstract:Covering: 1993 to 2002The synthesis of eribulin mesylate from microgram to multi-gram scale is described in this Highlight. Key coupling Reactions include formation of the C30a to C1 carbon–carbon bond and macrocyclic ring closure through an intramolecular Nozaki–Hiyama–Kishi Reaction.
Subrata Shaw - One of the best experts on this subject based on the ideXlab platform.
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cis‐2,5‐Diaminobicyclo[2.2.2]octane, a New Scaffold for Asymmetric Catalysis via Salen—Metal Complexes.
ChemInform, 2011Co-Authors: James D. White, Subrata ShawAbstract:Chromium-salen complex (I) is applied to the asymmetric hetero Diels—Alder Reaction of (II) with aldehydes and to the asymmetric Nozaki—Hiyama—Kishi Reaction of allyl bromide or chloride with aldehydes.
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cis-2,5-Diaminobicyclo[2.2.2]octane, a new scaffold for asymmetric catalysis via salen-metal complexes.
Organic Letters, 2011Co-Authors: James D. White, Subrata ShawAbstract:A new C2 symmetric salen scaffold based on cis-2,5-diaminobicyclo[2.2.2]octane has been synthesized that forms complexes with a wide range of metals. The chromium(III) complex is shown to catalyze the hetero-Diels−Alder Reaction and the Nozaki−Hiyama−Kishi Reaction with high efficiency and excellent stereoselectivity.
Mauricio M. Victor - One of the best experts on this subject based on the ideXlab platform.
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Stereoselectivity in the intramolecular Nozaki–Hiyama–Kishi Reaction: influence of the substitution pattern and protecting groups in the construction of 10-membered lactones
Tetrahedron Letters, 2002Co-Authors: Ronaldo A. Pilli, Mauricio M. VictorAbstract:Abstract The use of the intramolecular Nozaki–Hiyama–Kishi Reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C3 and C4 and the presence of the methyl group at C9 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. Matched induction led to the preparation of the decanolide moiety with high degree of stereoselection.
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The stereochemistry of the Nozaki-Hiyama-Kishi Reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D
Journal of the Brazilian Chemical Society, 2001Co-Authors: Ronaldo A. Pilli, Mauricio M. VictorAbstract:The use of the intramolecular Nozaki-Hiyama-Kishi Reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C4 and C5 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. The utility of this methodology has been demonstrated in the stereoselective total synthesis of (-)-decarestrictine D from 1,3-propanediol and polyhydroxybutyrate (PHB) in 13 steps and 6.3% overall yield.
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Total synthesis of (−)-decarestrictine D through a stereoselective intramolecular Nozaki-Hiyama-Kishi Reaction
Tetrahedron Letters, 1998Co-Authors: Ronaldo A. Pilli, Mauricio M. VictorAbstract:Abstract A concise total synthesis of (−)-decarestrictine D (1) from 1,3-propanediol and polyhydroxybutyrate (PHB) is described. The approach involves the stereoselective intramolecular Nozaki-Hiyama-Kishi coupling to construct the decanolide ring and to set the proper configuration at C-7.
Debendra K. Mohapatra - One of the best experts on this subject based on the ideXlab platform.
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The protecting-group directed diastereoselective Nozaki–Hiyama–Kishi (NHK) Reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues
Org. Biomol. Chem., 2014Co-Authors: Debendra K. Mohapatra, D. Sai Reddy, N. Arjunreddy Mallampudi, Janardhan Gaddam, Sowjanya Polepalli, Nishant Jain, J. S. YadavAbstract:The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki–Hiyama–Kishi (NHK) Reaction, De Brabander's lactonization Reaction and CBS reduction as the key steps. In this article, we have observed the most suitable protecting groups with respect to selectivity during the protecting group directed intermolecular asymmetric Nozaki–Hiyama–Kishi Reaction. The zeaenol, 7-epi-zeaenol and its derivatives were analyzed for their biological activity and screened in four cancer cell lines.
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Protecting‐Group Directed Stereoselective Intramolecular Nozaki–Hiyama–Kishi Reaction: A Concise and Efficient Total Synthesis of Amphidinolactone A (Eur. J. Org. Chem. 25/2010)
European Journal of Organic Chemistry, 2010Co-Authors: Debendra K. Mohapatra, Pragna P. Das, Manas R. Pattanayak, Gaddamanugu Gayatri, G. Narahari Sastry, J. S. YadavAbstract:The cover picture shows shows how a bulky protecting group directs the intramolecular Nozaki–Hiyama–Kishi Reaction to afford exclusively one stereoisomer, whereas a small protecting group directs the Reaction to afford both anti and syn isomers in a 2:1 ratio. Details are discussed in the article by D. K. Mohapatra, J. S. Yadav et al. on p. 4775 ff.
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Protecting-group directed stereoselective intramolecular Nozaki-Hiyama-Kishi Reaction: a concise and efficient total synthesis of amphidinolactone A
European Journal of Organic Chemistry, 2010Co-Authors: Debendra K. Mohapatra, Pragna P. Das, Manas R. Pattanayak, Gaddamanugu Gayatri, G. Narahari Sastry, Jhillu S. YadavAbstract:A convergent total synthesis of amphidinolactone A, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp., is described in 13 linear steps. The key step in the synthetic sequence involves an intramolecular Nozaki― Hiyama―Kishi (NHK) Reaction for the construction of the 13-membered lactone ring by union of two fragments derived from a single chiral epoxide. The stereochemical outcome of the NHK Reaction has been supported by computational studies.