HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Special Issue
Yoshito Kishi's Special Issues, Vol. 72, No. 1, 2007
Published online: 11th July, 2006
■ Ajmalinimine Is an Artifact Not an Alkaloid
Mauri Lounasmaa* and Pirjo Sainio (née Hanhinen)
*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, FIN-02150, HUT Espoo, Finland
Abstract
It is suggested that ajmalinimine (1), isolated from Rauwolfia serpentina Benth, is an artifact formed from 17-O-acetylajmaline (2) during the isolation and/or purification procedure.
Published online: 28th July, 2006
■ Parviflorene J, a Cytotoxic Sesquiterpene Dimer with a New Rearranged Skeleton from Curcuma parviflora
Mayu Tamaki, Samir Kumar Sadhu, Takashi Ohtsuki, Kazufumi Toume, Takashi Koyano, Thaworn Kowithayakorn, Masahiko Hayashi, Kanki Komiyama, and Masami Ishibashi*
*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
A new sesquiterpenoid dimer, parviflorene J, was isolated from Curcuma parviflora. The structure was elucidated using spectroscopic methods. Parviflorene J possessed an unprecedented backbone-rearranged skeleton and showed cytotoxicity against cultured tumor cell lines.
Published online: 22nd December, 2006
■ Cytotoxic Haterumadienone Congeners from the Okinawan Marine Sponge Dysidea Sp.
Katsuhiro Ueda,* Takayuki Ogi, Atsushi Sato, Eric R. O. Siwu, Masaki Kita, and Daisuke Uemura
*Department of Chemistry, Biology and Marine Sciences, Faculty of Science, University of Ryukyus, Nishihara-cho, Okinawa 903-0213, Japan
Abstract
20-Hydroxyhaterumadienone (1) and haterumadienelactol (2), new haterumadienone (3) congeners, were isolated from the sponge Dysidea sp. together with puupehenone (6) and three known metabolites (7-9) related to 6. The absolute stereochemistry of 1 and the relative stereochemistry of 2 were determined by spectroscopic and chemical analyses. The metabolites (1 and 2) inhibited the division of fertilized sea urchin eggs.
Published online: 6th February, 2007
■ Palladium-Catalyzed Coupling Reaction of Haloheteroaromatic Compounds in Water
Naoki Inoue, Osamu Sugimoto,* and Ken-ichi Tanji*
*Laboratory of Organic Chemistry, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan
Abstract
Palladium-catalyzed coupling reaction of π-deficient heteroaromatic halide in water was accomplished with excellent to good yields without any side reactions such as hydrolysis.
Published online: 29th December, 2006
■ Biosynthesis of Cypridina Luciferin in Cypridina noctiluca
Shin-ichi Kato, Yuichi Oba,* Makoto Ojika, and Satoshi Inouye
*Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan
Abstract
Luminescence in the marine ostracods Cypridina noctiluca and Vargula hilgendorfii is produced by Cypridina luciferin-luciferase reaction. In this study, a feeding experiment with stable isotope-labeled amino acids was performed in C. noctiluca. The results of LC/ESI-MS analyses indicated that C. noctiluca is able to synthesize Cypridina luciferin de novo from three amino acids (L-tryptophan, L-isoleucine, and L-arginine).
Published online: 26th December, 2006
■ Practical Approach for Hydroheteroarylation of Alkynes Using Bench-Stable Catalyst
Kyalo Stephen Kanyiva, Yoshiaki Nakao,* and Tamejiro Hiyama*
*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-katsura, Nishikyo, Kyoto 615-8510, Japan
Abstract
A simple and convenient method for hydroheteroarylation of alkynes using air-stable catalyst precursors is described. The addition of a solution of AlMe3 in hexane to Ni(acac)2 and tri(cyclopentyl)phosphonium tetrafluoroborate ([Cyp3PH]BF4) rapidly generates an active Ni(0)/Cyp3P catalyst for cis-hydroheteroarylation of alkynes under mild conditions. The catalytic reaction is applicable to a wide range of heteroarenes to give heteroaryl-substituted ethenes in excellent stereo- and regioselectivities.
Published online: 6th February, 2007
■ Synthesis of Enantiomerically Enriched 2-Substituted Pyrrolidine Analogues of Norhygrine. Applicatin of the Hetero-Diels-Alder Addition of Sulfur Dioxide
Mãris Turks and Pierre Vogel*
*Laboratory of Glycochemistry and Asymmetric Synthesis, ISIC, Swiss Federal Institute of Technology (EPFL), CH-1015 Lausanne, Switzerland
Abstract
The Vogel’s reaction cascade (one-pot hetero-Diels-Alder addition of SO2, ionization of the sultines into zwitterions and their quenching by electron-rich alkenes) has been applied to the preparation of enantiomerically-enriched (1S)-2((2R)-1-benzoylpyrrolidin-2-yl)pentan-3-one (14). Reaction of SO2 with (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-ol benzoate (5: derived from (S)-1-phenylethanol (97% ee)) and allyltrimethylsilane in the presence of a Lewis acid at -78°C provides (-)-(2Z,1’S,4S,5S)-4-methyl-5-(1’-phenylethoxy)octa-2,7-dien-3-ol benzoate (9). Selective cleavage of the benzyl ether of 9 and subsequent SN2 displacement with Ph2P(O)N3 provided an azide 11 that was converted into 14.
Published online: 9th March, 2007
■ Diastereodifferentiating [4+2]-Photocycloaddition of Tegafur with Naphthalene
Kazue Ohkura,* Tatsuyuki Sugaoi, Masayuki Takahashi, and Koh-ichi Seki*
*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan
Abstract
Upon UV-irradiation, the prodrug of 5-fluorouracil, tegafur, that has an asymmetric carbon attached to N1 couples with naphthalenes by way of stereoselective [4+2]-cycloaddition, to give the corresponding ethenoquinazolines as diastereoisomers. The configuration of the resulting adducts is unambiguously derived from X-ray crystal structural analysis.
Published online: 16th February, 2007
■ Regioselective Synthesis of Methyl 3-Thiothiophene-2-carboxylate Derivatives Utilizing a Dehydration-Type Ti-Dieckmann Condensation
Ryohei Nagase, Hideki Gotoh, Mayumi Katayama, Naoki Manta, and Yoo Tanabe*
*School of Science, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
Abstract
Regioselective dehydration-type Ti-Dieckmann condensation of 3-(methoxycarbonylmethylthio)propanethioates successfully afforded methyl thiophene-2-carboxylates and methyl 4,5-dihydrothiophene-2-carboxylates, utilizing TiCl4 - Et3N and TiCl4 - (sec-Bu)2NH, respectively.
Published online: 2nd March, 2007
■ Catalytic Enantioselective Aziridination of Alkenes Using Chiral Dirhodium(II) Carboxylates
Minoru Yamawaki, Masahiko Tanaka, Takumi Abe, Masahiro Anada, and Shunichi Hashimoto*
*Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan
Abstract
The enantioselective aziridination of alkenes with [N-(4-nitrophenylsulfonyl)imino]phenyliodinane catalyzed by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, is described. While such enantioselectivities are highly dependent on the properties of the alkenes, 2,2-dimethylchromene was found to be a particularly suitable substrate which can be efficiently transformed into the aziridine product in 98% yield with 94% ee.