The Journal of Organic Chemistry: Volume 58, Issue 8 (ACS Publications)

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April 1993

Volume 58, Issue 8

Pages 1985-2344

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Articles

A bridged tetrahydrophosphole ylide derived from 9-phenylphosphabicyclo[4.2.1]nonane: a reagent for E-selective Wittig reactions

E. Vedejs, M. J. Peterson

pp 1985–1986

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a001

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1,2- and 1,3-Monoazabisylides as novel synthons

Alan R. Katritzky, Jinlong Jiang, John V. Greenhill

pp 1987–1988

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a002

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Carbon acidity. 85. Ion pair acidities of 9,9'-bifluorenyl in THF: pK2 is lower than pK1

Manolis Stratakis, Andrew Streitwieser

pp 1989–1990

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a003

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Asymmetric dihydroxylation of olefins with a simple chiral ligand

Stephen Hanessian, Patrick Meffre, Mario Girard, Serge Beaudoin, Jean Yves Sanceau, Youssef Bennani

pp 1991–1993

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a004

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Spirodienone route for aminodehydroxylation: monoaminotrihydroxy-p-tert-butylcalix[4]arene

Oleg Aleksiuk, Flavio Grynszpan, Silvio E. Biali

pp 1994–1996

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a005

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Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

Takuya Yamamoto, Seigo Ishibuchi, Tadao Ishizuka, Mamoru Haratake, Takehisa Kunieda

pp 1997–1998

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a006

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Synthesis of lithio-F-adamantanes: the first documented fluorine-19 NMR spectrum of a perfluoroalkyllithium and the rearrangement of 2-lithio-F-adamantane to 1-lithio-F-adamantane

James L. Adcock, Huimin Luo

pp 1999–2000

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a007

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Characterization of a triazine (2-[(3-amino-1,2,4-triazin-5-yl)methylene]hydrazinecarboximideamide) formed from glucose and aminoguanidine under oxidative conditions

James A. Blackledge, Min Xin Fu, Suzanne R. Thorpe, John W. Baynes

pp 2001–2002

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a008

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Electron-transfer rate determinations: facile electron transfer from 1,1,2,2-tetrakis(4-methoxyphenyl)ethanediol

John H. Penn, Joseph H. Duncan

pp 2003–2008

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a009

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Efficient synthesis of alkoxyanthraquinones from fluoroanthraquinones and their preliminary electrochemistry

L. Echegoyen, Yehia Hafez, Raphael C. Lawson, J. de Mendoza, T. Torres

pp 2009–2012

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a010

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Reactions of ferrocene and acetylferrocene with carbon-centered free radicals

Enrico Baciocchi, Barbara Floris, Ester Muraglia

pp 2013–2016

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a011

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Structure of the cyclopropane cation radical and its energy barrier to pseudorotation

Charles E. Hudson, C. S. Giam, David J. McAdoo

pp 2017–2019

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a012

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Electronic structure of benzo[3,4]cyclobuta[1,2]cycloheptenyl ions: the aromaticity-tropicity dilemma

Ulf Edlund, Dan Johnels, Bertil Eliasson, Lars Trogen

pp 2020–2024

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a013

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Inter- versus intramolecular cyclobutadiene complex formation in the reaction of 1,6-cyclodecadiyne derivatives with (.eta.5-Me5C5)Co(C2H4)2

Rolf Gleiter, Roland Merger, Hermann Irngartinger, Bernhard Nuber

pp 2025–2028

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a014

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Intrinsic reactivity of sulfur esters: site selectivity by anions with dimethyl sulfate and methyl methanesulfonate

Rachel C. Lum, Joseph J. Grabowski

pp 2029–2034

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a015

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Electron-transfer photochemistry of thianthrene. Nucleophile-assisted photooxidation to sulfoxide

Guilford Jones II, Bin Huang, Susan F. Griffin

pp 2035–2042

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a016

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Theoretical study of conformational features of NAD+ and NADH analogs: protonated nicotinamide and 1,4-dihydronicotinamide

Yun Dong Wu, K. N. Houk

pp 2043–2045

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a017

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Syntheses and properties of 5-substituted [n](2,4)pyridinophanes, model compounds of NAD(P)

Tadayoshi Oikawa, Nobuhiro Kanomata, Masaru Tada

pp 2046–2051

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a018

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A stereocontrolled alkylation of chiral pyridinium salts with Grignard reagents: synthesis of (+)-normetazocine and (+)-nordextrorphan

Yves Genisson, Christian Marazano, Bhupesh C. Das

pp 2052–2057

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a019

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Acid-mediated reaction of bis(pyridine)iodonium(I) tetrafluoroborate with aromatic compounds. A selective and general iodination method

Jose Barluenga, Jose M. Gonzalez, Miguel A. Garcia-Martin, Pedro J. Campos, Gregorio Asensio

pp 2058–2060

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a020

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Cycloaddition of (phenylsulfonyl)-1,2-propadienes with diazomethane. Novel rearrangement reactions of the resulting cycloadducts

Albert Padwa, Michelle A. Filipkowski, Donald N. Kline, S. Shaun Murphree, Philip E. Yeske

pp 2061–2067

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a021

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4.pi. Participation of 1-aza-1,3-butadienes in [4 + 2] cycloaddition reactions: intramolecular Diels-Alder reactions of .alpha.,.beta.-unsaturated N-sulfonylimines

Dale L. Boger, Wendy L. Corbett

pp 2068–2074

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a022

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Diels-Alder reaction of 2-cyano-1-azadienes. The effect of nitrogen substituents

Celine Trione, Leticia M. Toledo, Scott D. Kuduk, Frank W. Fowler, David S. Grierson

pp 2075–2080

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a023

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Palladium(II)-promoted cross-coupling of 4-alkenyl-2-azetidinones with organomercurials

Richard C. Larock, Shuji Ding

pp 2081–2085

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a024

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The conversion of secondary into tertiary amides using benzotriazole methodology

Alan R. Katritzky, Guowei Yao, Xiangfu Lan, Xiaohong Zhao

pp 2086–2093

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a025

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Strong inhibition of cis-trans isomerization of azo compounds by hydroxide ion

Ana Sanchez, Rita H. De Rossi

pp 2094–2096

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a026

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Acid-catalyzed decomposition of 1-alkyltriazolines: a mechanistic study

Richard H. Smith Jr., Brian D. Wladkowski, Jesse E. Taylor, Erin J. Thompson, Brunon Pruski, John R. Klose, A. W. Andrews, Christopher J. Michejda

pp 2097–2103

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a027

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The triazene moiety as a protecting group for aromatic amines

Margaret L. Gross, David H. Blank, Willard M. Welch

pp 2104–2109

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a028

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Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

Ernest W. Della, Andrew M. Knill, Paul E. Pigou

pp 2110–2114

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a029

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Aryl radical cyclizations onto enamine double bonds

Stephen A. Glover, John Warkentin

pp 2115–2121

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a030

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Reversible formation of bromonium ions. Preferential reaction of Br- on the Br+ of the bromonium ion produced from the solvolysis of trans-2-bromocyclohexyl triflate in methanol or acetic acid containing added bromide

C. Y. Zheng, H. Slebocka-Tilk, R. W. Nagorski, L. Alvarado, R. S. Brown

pp 2122–2127

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a031

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Mixed anhydrides: physical properties influenced by molecular structure

John H. Penn, Walter H. Owens, Jeffrey L. Petersen, Harry O. Finklea, Daniel A. Snider

pp 2128–2133

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a032

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Reactivity of tricarbonyl(pentadienyl)iron(1+) cations: enantioselective synthesis of 5-HETE methyl ester

Chunlin Tao, William A. Donaldson

pp 2134–2143

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a033

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Conjugate-addition reactions of .alpha.-sulfinyl ketimine anions with a methyl .alpha.-amidoacrylate. Concise asymmetric total syntheses of (-)-slaframine and (-)-6-epislaframine

Duy H. Hua, Jewn Giew Park, Takeshi Katsuhira, S. Narasimha Bharathi

pp 2144–2150

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a034

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A highly diastereo- and enantioselective synthesis of the top half of kijanolide

William R. Roush, Bradley B. Brown

pp 2151–2161

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a035

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Studies on the synthesis of kijanolide: synthesis of the 2-acyl spirotetronate and investigations concerning the coupling of the top and bottom half fragments

William R. Roush, Bradley B. Brown

pp 2162–2172

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a036

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Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

Janet A. Gaboury, Mukund P. Sibi

pp 2173–2180

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a037

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Total synthesis of natural gingerols, the three active principles of ginger

Guy Solladie, Chewki Ziani-Cherif

pp 2181–2185

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a038

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Cycloaddition routes to tricyclo[5.4.01,7.02,9]undecanes: a direct total synthesis of (+)-longifolene via an intramolecular Diels-Alder strategy

Bo Lei, Alex G. Fallis

pp 2186–2195

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a039

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Cleavage of unsaturated .alpha.-ketols to .omega.-oxo-.alpha.,.beta.-unsaturated acids

Rey Floresca, Masaaki Kurihara, David S. Watt, Ayhan Demir

pp 2196–2200

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a040

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Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates

Takayuki Ohe, Norio Miyaura, Akira Suzuki

pp 2201–2208

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a041

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Synthesis of the 60 amino acid homeo domain and smaller fragments of the Drosophila gene regulatory protein Antennapedia by a segment synthesis-condensation approach

Hisakazu Mihara, Jean A. Chmielewski, Emil T. Kaiser

pp 2209–2215

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a042

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Synthesis of a 39-peptide and a 25-peptide by thiol capture ligations: observation of a 40-fold rate acceleration of the intramolecular O,N-acyl-transfer reaction between peptide fragments bearing only cysteine protective groups

D. S. Kemp, Robert I. Carey

pp 2216–2222

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a043

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The synthesis of oligonucleotide-polyamide conjugate molecules suitable as PCR primers

Glenn Tong, John M. Lawlor, Geoffrey W. Tregear, Jim Haralambidis

pp 2223–2231

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a044

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Chemical synthesis and characterization of duplex DNA containing a new base pair: a nondisruptive, benzofused pyrimidine analog

Marjorie S. Solomon, Paul B. Hopkins

pp 2232–2243

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a045

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NADV: a new cofactor for alcohol dehydrogenase from Thermoanaerobium brockii

Debbie C. Crans, Robert W. Marshman, Rikke Nielsen, Irena Felty

pp 2244–2252

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a046

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Biocatalytic production of glyoxylic acid

John E. Seip, Susan K. Fager, John E. Gavagan, Lawrence W. Gosser, David L. Anton, Robert DiCosimo

pp 2253–2259

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a047

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Reduction of 2-substituted 3-oxoglutarates mediated by baker's yeast. Variation in enantioselectivity without corresponding variation in diastereoselectivity

Tuncer Arslan, Steven A. Benner

pp 2260–2264

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a048

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Selective urea transport by macrocyclic carriers through a supported liquid membrane

Wilma F. Van Straaten-Nijenhuis, Arie R. Van Doorn, Arjen M. Reichwein, Feike De Jong, David N. Reinhoudt

pp 2265–2271

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a049

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Phosphonates as mimics of phosphate biomolecules: ab initio calculations on tetrahedral ground states and pentacoordinate intermediates for phosphoryl transfer

Gregory R. J. Thatcher, A. Stewart Campbell

pp 2272–2281

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a050

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Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid

Eusebio Juaristi, Jaime Escalante

pp 2282–2285

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a051

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A short stereocontrolled synthesis of hydroxyethylene dipeptide isosteres

D. Michael Jones, Bo Nilsson, Michael Szelke

pp 2286–2290

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a052

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New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses

Caroline Chauvin, Krystyna Baczko, Daniel Plusquellec

pp 2291–2295

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a053

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A synthetic approach to 3-substituted cephalosporins: carbon-carbon bond formation at C(3) of the cephem via organocuprate chemistry

Joydeep Kant

pp 2296–2301

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a054

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A remarkably simple route to versatile difluoromethylated molecules

Sadanori Kaneko, Takashi Yamazaki, Tomoya Kitazume

pp 2302–2312

Publication Date: April 1993 (Article)

DOI: 10.1021/jo00060a055

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An effective synthesis of N-(9-fluorenylmethyloxycarbonyl) .alpha.-amino aldehydes from S-benzyl thioesters

Pak T. Ho, Kheh Yong Ngu

pp 2313–2316

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a056

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Synthesis of 4-(1-propynyl)-1-(5-hexene-1,3-diynyl)-1,3-cyclohexadiene and 4-(1-propynyl)-1-(4-(trimethylsilyl)-1,3-butadiynyl)-1,3-cyclohexadiene

Fillmore Freeman, Darrick S. H. L. Kim, Eloy Rodriguez

pp 2317–2319

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a057

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Thermal fragmentation reactions of dihydroaromatic molecules

Bernard Miller, Xiaolian Shi, George Grosu, Renmo Zhou

pp 2320–2323

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a058

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Mercuric iodide as an exceptionally mild catalyst for the condensations of silyl ketene acetals with electrophiles

Ira B. Dicker

pp 2324–2327

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a059

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Syntheses of exo-3,8-dioxatricyclo[3.2.1.02,4]octane and 4,7-dioxatricyclo[3.2.1.03,6]octane and the relative basicities of their ethereal moieties

Claude le Drian, Pierre Vogel

pp 2328–2330

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a060

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Unusual oxidation of 1-halo-1,3-dienes with parmanganate. Expedient syntheses of (+)-D-chiro-3-inosose and (+)-D-chiro-inositol from chlorobenzene

Martin Mandel, Tomas Hudlicky, Lawrence D. Kwart, Gregg M. Whited

pp 2331–2333

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a061

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Synthesis and crystal structure of a peptidomimetic containing the (R)-4.4-spiro lactam type-II .beta.-turn mimic

Michael J. Genin, William H. Ojala, William B. Gleason, Rodney L. Johnson

pp 2334–2337

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a062

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Improved synthesis of 24-epibrassinolide from ergosterol

Trevor C. McMorris, Prakash A. Patil

pp 2338–2339

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a063

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Synthesis of the first .alpha.-linked quaterpyrrole

Hidetsugu Ikeda, Jonathan L. Sessler

pp 2340–2342

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a064

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Synthesis and hydrolysis kinetics of 1-O-[p-(N,N,N-trimethylammonio)phenyl]-.beta.-D-ribofuranoside

David H. Vance, Anthony W. Czarnik

pp 2343–2344

Publication Date: April 1993 ()

DOI: 10.1021/jo00060a065

First Page

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