Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
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Volume 72, Issue 10
Displaying 1-12 of 12 articles from this issue
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Preface
Reviews and Accounts
  • Synthesis of P-Chiral Phosphine Ligands and Their Applications in Asymmetric Catalysis
    Tsuneo Imamoto, Masashi Sugiya, Nobuhiko Oohara, Ken Tamura
    2014 Volume 72 Issue 10 Pages 1084-1096
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1084
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    This review describes the recent progress of the synthesis of P-chiral phosphine ligands and their applications in transition-metal-catalyzed asymmetric reactions. Many enantiomerically pure P-chiral phosphine ligands have been prepared by the use of phosphine-boranes as the intermediates. Among the ligands prepared hitherto, the bidentate ligands with tert-butyl groups at the phosphorus atoms exhibit remarkably high enantioinduction ability in many catalytic asymmetric reactions, particularly in rhodium-catalyzed hydrogenations. Both enantiomers of air-stable ligands, QuinoxP* and BenzP*, are produced via (R)- and (S)-tert-butylmethylphosphine-boranes. These two ligands have been successfully used not only in asymmetric hydrogenations but also in enantioselective carbon-carbon or carbon-heteroatom bond-forming reactions. Many other P-chiral phosphine ligands reported since 2001 are also described.
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  • Discovery of Anti-influenza Drug, Laninamivir Octanoate (Inavir®)
    Yoshiyuki Kobayashi, Takeshi Honda, Takeshi Masuda, Masami Arai
    2014 Volume 72 Issue 10 Pages 1097-1109
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1097
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    Laninamivir Octanoate (Inavir®) (1) is the long-acting anti-influenza drug, and has been launched in 2010. It is the prodrug of laninamivir (2), which is a neuraminidase inhibitor, and it shows the clinically interesting drug profile such as “single inhaled administration for the treatment of influenza”. Herein, we describe the synthetic aspects for the drug discovery program on Laninamivir Octanoate (Inavir®) (1) and its related compounds, featuring 1) the introduction of fully-protected guanidyl group to C-4 position of laninamivir (2), 2) the synthesis of a variety of 7-modified sialic acids from 4-modified N-acetyl glucosamines and 4-modified N-acetyl mannnosamines via enzymatic aldol condensation using Neu5Ac aldolase, and 3) the development of direct alkylation to less reactive C-7 OH group of sialic acid. Also, we describe the topics on our derivatization diversified by these synthetic methods to discover Laninamivir Octanoate (Inavir®) (1).
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  • Nickel Catalysts Containing Bulky N-Heterocyclic Carbene Ligands: Syntheses, Structures and Catalytic Applications to Cross-Coupling Reactions
    Kouki Matsubara
    2014 Volume 72 Issue 10 Pages 1110-1119
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1110
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    Several new nickel complexes bearing bulky N-heterocyclic carbene (NHC) ligands were developed as highly active catalysts in order to achieve efficient cross-coupling reactions of aryl halides. These complexes were identified on the basis of NMR, IR, MS spectroscopy and determined by X-ray crystallography. It should be noted that the steric requirements of the most bulky carbene, IPr (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), controlled the reactivity of the nickel compounds to form catalytically active unsaturated species. That is, the NHC ligand stabilizes unusual paramagnetic or diamagnetic monovalent nickel compounds, which have performed high catalytic activity via a specific catalytic cycle between Ni(I)-Ni(I) and Ni(II)-Ni(II) species in the cross-coupling reactions. Kumada-Tamao-Corriu cross-coupling and Buchwald-Hartwig amination of aryl halides, and α-arylation of linear ketones were achieved to form corresponding coupling products in sufficient yields. In particular, amination with diarylamines proceeded efficiently under mild conditions to form triarylamine derivatives which are very important in optical or electronic organic devices, in contrast to the corresponding palladium chemistry.
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  • Alkaloid Synthesis by Means of Hypervalent Iodobenzene
    Tsuyoshi Saitoh, Shigeru Nishiyama
    2014 Volume 72 Issue 10 Pages 1120-1130
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1120
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    The novel organic iodine (III) reagent, phenyliodine bis(trifluoroethoxide) (PIFE), was developed by means of electrochemical oxidation process from iodobenzene. PIFE showed the great reactivity against amide derivatives such as methoxy and acyl anilide as well as commercially available organic iodine (III) reagents, and pH of its reaction media was almost neutral. The oxidative syntheses of azaspirodienone and quinolinone through the nitrenium ion were successfully achieved with PIFE. Moreover, oxidative ring closing reaction of biaryl acetoanilide was also achieved with PIFE not the presence of transition metal catalyst and provided several carbazole derivatives. During the course of our exploratory research for the scope and limitation of oxidative ring formation with PIFE, the authors developed the novel pyrolidinoindoline synthetic method by means of organic iodine (III) reagents.
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  • New Synthetic Approaches to Fused Polyheterocyclic Compounds by Using Domino Cyclization Reactions of Aromatic Diyne and Enyne Systems
    Ryo Irie, Masaki Furusawa, Kosuke Arita, Kazunobu Igawa, Katsuhiko Tom ...
    2014 Volume 72 Issue 10 Pages 1131-1142
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1131
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    Oxa-heterocyclic compounds such as benzofurans, chromenes, and chromanes constitute a diverse array of biologically active materials. Furthermore, extended π-conjugated systems, in which oxa-heteroaromatic and benzene rings are condensed alternately, have been exploited as components of photoelectronic devices. Thus, the development of efficient synthetic approaches toward these valuable classes of heterocycles has been pursued. Among those precedented heterocyclization methods, domino cyclodehydrogenation and cycloisomerization reactions are highly attractive as they could produce elaborate heterocyclic frameworks from readily available starting materials in an atom-efficient manner. Herein, we wish to report the novel multimode domino ring-forming reactions of o-phenylenediyne-linked bis(arenol)s (aromatic diyne systems) and its analogous aromatic enyne systems to provide unique fused oxa-heterocycles, which are otherwise difficult to synthesize.
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  • Construction of Ansa-skeleton via Intramolecular Dötz Benzannulation: Total Synthesis of Kendomycin
    Yoko Saikawa, Kyosuke Tanaka, Masaya Nakata
    2014 Volume 72 Issue 10 Pages 1143-1153
    Published: October 01, 2014
    Released on J-STAGE: November 17, 2014
    DOIhttps://doi.org/10.5059/yukigoseikyokaishi.72.1143
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    Ansa-compounds have intriguing molecular structures and highly potent bioactivities. One of the ansa-compounds, kendomycin, has an oxa-metacyclophane skeleton with quinone methide core and a fully substituted tetrahydropyran ring. In contrast to a common synthetic strategy for construction of the ansa-skeleton via elongation of an alkyl chain from an aromatic core followed by macrocyclization, we challenged a new method for construction of the ansa-skeleton via simultaneous macrocyclization and benzannulation (using intramolecular Dötz benzannulation). Understanding the reactivity of various Fischer-type ω-alkynyloxy chromium carbene complexes with kendomycin analogs syntheses led to achievement of the total synthesis of kendomycin. Investigations of structure-activity relationships revealed the need for an ansa-skeleton for antimicrobial activity.
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Review de Debut
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