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摘要

ISSN 0300-922X JCPRB4(5) 845-1078(1989) 845 85 1 857 867 973 879 887 897 905 909 915 919 925 93 1 935 945 JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS A new route to optically active (4R)-2-substituted 4-hydroxycyclopent-2-enones from D-glucose Elisabetta Mezzina, Diego Savoia, Emilio Tagliavini, Claudio Trombini, and Achille Umani-Ronchi Studies of precursor-directed biosynthesis with streptomyces. Part 2. New and unusual manumycin analogues produced by Streptomyces parvulus Ralf Thiericke, Hans-Jorg Langer, and Axel Zeeck Model studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: synthesis of prolyl peptides via a four-component condensation Margaret M.Bowers, Patrick Carroll, and Madeleine M. JoulliC Improvement in the enantioselectivity of the hydrogen transfer with NADH models bearing amino alcohols as chiral auxiliaries Jacques Cazin, Jack Duflos, Georges Dupas, Jean Bourguignon, and Guy QuCguiner Structural studies of FR900359, a novel cyclic depsipeptide from Ardisia crenata Sims (Myrsinaceae) Akira Miyamae, Mamoru Fujioka, Shigetaka Koda, and Yukiyoshi Morimoto Synthesis of five-membered lactams by a-carbamoyl radical cyclisations Tatsunori Sato, Yasuko Wada, Mami Nishi- moto, Hiroyuki Ishibashi, and Masazumi Ikeda Trichothecene mycotoxin interconversions: partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3~,4~,15-triacetoxy-12,13-epi-epoxytrichothec-9-eneStuart Cameron and Ernest W.Colvin Asymmetric syntheses of chiral propane-1,3-diols starting from malonic acid Masataka Ihara, Masanobu Takahashi, Nobuaki Taniguchi, Ken Yasui, Keiichiro Fukumoto, and Tetsuji Kametani Quinoline alkaloids. Part 26. Pseudobases from the reaction of furoquinolinones with methyl iodide. A new route to 3-(3-methyI-2-oxobutyl)quinolin-2(1H)-ones John L. Gaston and Michael F. Grundon Perfluoroalkylations of nitrogen-containing heteroaromatic compounds with bis(perfluoroalkanoy1) peroxides Masato Yoshida, Tatsuro Yoshida, Michio Kobayashi, and Nobumasa Kamigata Addition of 0-alkyl 0’-trimethylsilyl ketene acetals to arynes generated from several aryl halides with NaNH2 Syed Masarrat Ali and Shigeo Tanimoto Phosphorylated sugars.Part 25. Synthesis and behaviour in acidic media of 2-acetamido-2-deoxy-~-glucose4- and 6-phosphates and of a ‘Lipid A’ analogue Patricia Szabb C-Nucleoside studies. Part 20. Synthesis of some pyrazolo[4,3-d]pyrimidine acyclonucleosides related to (S)-(2,3,di- hydroxypropy1)adenine; a direct method for double functionalization of the pyrazole ring J. Grant Buchanan, Mark Harrison, Richard H. Wightman, and Michael R.Harnden Synthesis of o-substituted phenols by Criegee rearrangement of benzylic hydroperoxides Benjamin Taljaard, AndrC Goosen, and Cedric W. McCleland Highly enantiospecific synthesis of 4-alkyl and 4,Sdialkyl substituted 4,5-dihydrofuran-2(3H)-ones from optically active (E)-and (2)-alk- 1-enyl p-tolyl sulphoxides: application to the synthesis of lignan lactones Hiroshi Kosugi, Katsuya Tagami, Akira Takahashi, Hiroshi Kanna, and Hisashi Uda Heterocyclic mesomeric betaines.Part 1. Synthesis and cycloaddition reactions of hetero derivatives of the phenalenide anion W. David Ollis, Stephen P.Stanforth, and Christopher A. Ramsden 1 CONTENTS 953 Heterocyclic mesomeric betaines. Part 2. Synthesis of a hetero derivative of the benzo[b]phenalenide anion W. David Ollis, Stephen P. Stanforth, and Christopher A. Ramsden 957 Heterocyclic mesomeric betaines. Part 3. Synthesis and base-catalysed exchange reactions of N-methyl-5H-pyrrolo- [1,2-c]imidazolium iodide W. David Ollis, Stephen P. Stanforth, and Christopher A. Ramsden 96 I Heterocyclic mesomeric betaines. Part 4.Reductive cyclization of derivatives of 7-methyl-2-(2 -nitrophenyl)imidazo- [1,2-a]pyridine W. David Ollis, Stephen P. Stanforth, and Christopher A. Ramsden 965 Heterocyclic mesomeric betaines. Part 5. Synthesis and cycloaddition reactions of hetero derivatives of the 2-methylene- 1,2-dihydro- 1,3-~henalenylene dianion W. David Ollis, Stephen P. Stanforth, and Christopher A. Ramsden 969 Synthesis of capped oligoribonucleotides by use of protected 7-methylguanosine 5’-diphosphate derivatives Mitsuo Sekine, Reiko Iwase, Tsujiaki Hata, and Kin-ichiro Miura 979 A new acylative cycloaddition reaction John Knight and Philip J. Parsons 985 The use of dichloromaleic and bromomaleic anhydrides in the synthesis of lactones by the intramolecular Diels-Alder reaction Mark J.Batchelor and John M. Mellor 997 Synthesis of hydroisoindoles via intramolecular Diels-Alder reactions of functionalised amido trienes John M. Mellor and Alison M. Wagland 1007 Reaction of (E)-P-enamino amides with dimethyl acetylenedicarboxylate (DMAD): formation of benzene derivatives, enamino esters, and 2-pyridones Antonio Nuvole and Giuseppe Paglietti 1013 Synthetic studies on antibiotic validamycins. Part 13. Total synthesis of (+)-validamycins A and E, and related com- pounds Yasunobu Miyamoto and Seiichiro Ogawa 1019 On the reactivity of tricarbonyl( 14-q-cyclohepta- 1,3,5-triene)iron derivatives: C-C bond formation of tricarbonyl- (cyc1oheptatrienide)irons with 2-chlorotropone Makoto Nitta, Masaki Nishimura, and Hiroyuki Miyano 1025 Regio, diastereo-, and enantio-selective condensation of chiral vinylic borates with aldehydes Tiziana Basile, Stefan0 Biondi, Gian Paolo Boldrini, Emilio Tagliavini, Claudio Trombini, and Achille Umani-Ronchi 1031 Synthesis and reaction of 1,2,4-trioxanes Tomohiro Fujisaka, Masahiro Miura, Masatomo Nojima, and Shigekazu K usa bay as hi 1041 Synthesis and stereoselective reactions of 2-(pyrrol-1-yl)alkanals and 2-(pyrrol- 1 -yl)alkan- 1 -ones Choji Kashima, Tatsuya Maruyama, Yoko Fujioka, and Kazuo Harada 1047 Natural products chemistry.Part 124. Revised structure and synthesis of a new acridone alkaloid, hallacridone from Ruta gruveolens tissue cultures Johannes Reisch and G. M. Kamal B. Gunaherath 1053 Reaction of ketone alkylhydrazones with phosphorus trichloride: a general mild route to substituted pyrroles Graziano Baccolini 1057 Enzymatic synthesis of various 1’-0-sucrose and 1 -0-fructose esters Giacomo Carrea, Sergio Riva, Francesco Secundo, and Bruno Danieli Perkin Communication 1063 An e.s.r.study of radical cation cyclization in the radiolytic oxidation of but-3-en-1-01 solutions in Freon matrices Sheng Dai, Jih Tzong Wang, and Ffrancon Williams 1065 Chiral quinuclidines (l-azabicyclo[2.2.2]octanes) from sugars: synthesis of (3S,5S)-quinuclidine-3,5-diol from D-arabi- nose George W. J. Fleet, Christopher J. Mathews, Julio A. Seijas, M. P. Vazquez Tato, and David J. Brown 1067 Complex quinuclidines (1 -azabicyclo[2.2.2]octanes) from sugars: synthesis of (1a,3a,4a,5a)-quinuclidine-3,5-diol from D-glucose George W.J. Fleet, Christopher J. Mathews, Julio A. Seijas, M. P. Vazquez Tato, and David J. Brown 1068 Key intermediates for the synthesis of organic semiconductors: a direct dithiocarbamate route to unsubstituted 1,3- dithiol-2-one derivatives Frank S. Guziec, Jr., Joseph M. RUSSO, Felix F. Torres, G. Cornell Long, and Mario R. Tellez 1070 Selective and continuous-flow mono-methylation of arylacetonitriles with dimethyl carbonate under gas-liquid phase- transfer catalysis conditions Pietro Tundo, Francesco Trotta, and Giovanni Moraglio 1071 Regiospecific ortho-lithiation of phthalocyanines: a route for one-step synthesis of highly soluble trimethylsilyl substituted phthalocyanines M.J. Chen, C. M. Fendrick, R. A. Watson, K. S. Kinter, and J. W. Rathke 1073 New water-soluble calixarenes bearing sulphonate groups on the ‘lower rim’: the relation between calixarene shape and binding ability Seiji Shinkai, Hirosuke Kawabata, Takashi Arimura, Tsutomu Matsuda, Hiroshi Satoh, and Osamu Manabe 1075 Partial synthesis and the absolute configuration of two new Gelsemium alkaloids, koumidine and (192)-taberpsychine Hiromitsu Takayama, Mariko Kitajima, Surnphan Wongseripipatana, and Shin-ichiro Sakai 11 CONTENTS Corrigendum 1077 Synthesis of novel labile rotenoids with unnatural trans-B/C ring systems Michael J. Begley, Leslie Crombie, A. Hamid bin A. Hadi, and Jonathan L. Josephs ... 111 AUTHOR INDEX Ah, Syed Masarrat, 915 Arimura, Takashi, 1073 Baccolini, Graziano, 1053 Basile, Tiziana, 1025 Batchelor, Mark J., 985 Begley, Michael J., 1077 Biondi, Stefano, 1025 Boldrini, Gian Paolo, 1025 Bourguignon, Jean, 867 Bowers, Margaret M., 857 Brown, David J., 1065, 1067 Buchanan, J.Grant, 925 Cameron, Stuart, 887 Carrea, Giacomo, 1057 Carroll, Patrick, 857 Cazin, Jacques, 867 Chen, M. J., 1071 Colvin, Ernest W., 887 Crombie, Leslie, 1077 Dai, Sheng, 1063 Danieli, Bruno, 1057 Duflos, Jack, 867 Dupas, Georges, 867 Fendrick, C. M., 1071 Fleet, George W. J., 1065, Fujioka, Mamoru, 873 Fujioka, Yoko, 1041 Fujisaka, Tomohiro, 1031 Fukumoto, Keiichiro, 897 Gaston, John L., 905 Goosen, Andre, 93 1 Grundon, Michael F., 905 Gunaherath, G.M. Kamal B., 1047 Guziec, Jr. Frank S., 1068 Hadi, A. Hamid bin A,, 1077 Harada, Kazuo, 1041 Harnden, Michael R., 925 Harrison, Mark, 925 Hata, Tsujiaki, 969 Ihara, Masataka, 897 Ikeda, Masazumi, 879 Ishibashi, Hiroyuki, 879 Iwase, Reiko, 969 Josephs, Jonathan L., 1077 Joullie, Madeleine M., 857 Kametani, Tetsuji, 897 Kamigata, Nobumasa, 909 Kanna, Hiroshi, 935 Kashima, Choji, 1041 Kawabata, Hirosuke, 1073 Kinter, K. S., 1071 Kitajima, Mariko, 1075 Knight, John, 979 Kobayashi, Michio, 909 Koda, Shigetaka, 873 Kosugi, Hiroshi, 935 Kusabayashi, Shigekazu, 1031 Langer, Hans-Jorg, 85 1 Long, G. Cornell, 1068 Manabe, Osamu, 1073 Maruyama, Tatsuya, 104 1 Mathews, Christopher J., 1065, 1067 Matsuda, Tsutomu, 1073 McCleland, Cedric W., 93 1 Mellor, John M., 985,997 Mezzina, Elisabetta, 845 Miura, Kin-ichiro, 969 Miura, Masahiro, 1031 Miyamae, Akira, 873 Miyamoto, Yasunobu, 1013 Miyano, Hiroyuki, 1019 Moraglio, Giovanni, 1070 Morimoto, Yukiyoshi, 873 Nishimoto, Mami, 879 Nishimura, Masaki, 1019 Nitta, Makoto, 1019 Nojima, Masatomo, 1031 Nuvole, Antonio, 1007 Ogawa, Seiichiro, 1013 Ollis, W.David, 945,953, 957, 96 1,965 Paglietti, Giuseppe, 1007 Parsons, Philip J., 979 Queguiner, Guy, 867 Ramsden, Christopher A., 945, 953,957,961,965 Rathke, J. W., 1071 Reisch, Johannes, 1047 Riva, Sergio, 1057 Russo, Joseph M., 1068 Sakai, Shin-ichiro, 1075 Sato, Tatsunori, 879 Satoh, Hiroshi, 1073 Savoia, Diego, 845 Secundo, Francesco, 1057 Seijas, Julio A., 1065, 1067 Sekine, Mitsuo, 969 Shinkai, Seiji, 1073 Stanforth, Stephen P., 945,953,957, 961,965 Szabo, Patricia, 919 Tagami, Katsuya, 935 Tagliavini, Emilio, 845, 1025 Takahashi, Akira, 935 Takahashi, Masanobu, 897 Takayama, Hiromitsu, 1075 Taljaard, Benjamin, 93 1 Taniguchi, Nobuaki, 897 Tanimoto, Shigeo, 9 15 Tato, M.P. Vazquez, 1065, 1067 Tellez, Mario R., 1068 Thiericke, Ralf, 851 Torres, Felix F., 1068 Trombini, Claudio, 845, 1025 Trotta, Francesco, 1070 Tundo, Pietro, 1070 Uda, Hisashi, 935 Umani-Ronchi, Achille, 845, 1025 Wada, Yasuko, 879 Wagland, Alison M., 997 Wang, Jih Tzong, 1063 Watson, R. A., 1071 Wightman, Richard H., 925 Williams, Ffrancon, 1063 Wongseripipatana, Sumphan, 1075 Yasui, Ken, 897 Yoshida, Masato, 909 Yoshida, Tatsuro, 909 Zeeck, Axel, 851 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence. iv