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Pure Appl. Chem., 1994, Vol. 66, No. 10-11, pp. 2119-2122

http://dx.doi.org/10.1351/pac199466102119

Enantiocontrolled route to natural products using chiral equivalents of cyclopentenone and cyclohexenone

K. Ogasawara

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  • Miklós Ferenc, Tóth Zita, Hänninen Mikko M., Sillanpää Reijo, Forró Enikő, Fülöp Ferenc: Retro-Diels-Alder Protocol for the Synthesis of Pyrrolo[1,2-a ]pyrimidine and Pyrimido[2,1-a ]isoindole Enantiomers. Eur. J. Org. Chem. 2013, 2013, 4887. <http://dx.doi.org/10.1002/ejoc.201300452>
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  • OGASAWARA K.: ChemInform Abstract: Enantiocontrolled Route to Natural Products Using Chiral Equivalents of Cyclopentenone and Cyclohexenone. ChemInform 2010, 26, no. <http://dx.doi.org/10.1002/chin.199507304>
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  • Klunder Antonius J.H., Volkers Andries A., Zwanenburg Binne: Facial selectivity in addition reactions to the highly strained enone in tricyclo[5.2.1.02,6]deca-2(6),8-dienone and tricyclo[5.2.1.02,6]dec-2(6)-enone. Tetrahedron 2009, 65, 2356. <http://dx.doi.org/10.1016/j.tet.2009.01.012>
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  • Larson Kimberly K., Sarpong Richmond: Total Synthesis of Alkaloid (±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction. J Am Chem Soc 2009, 131, 13244. <http://dx.doi.org/10.1021/ja9063487>
  • Soeta Takahiro, Selim Khalid, Kuriyama Masami, Tomioka Kiyoshi: Kinetic resolution of 5-substituted cycloalkenones by peptidic amidophosphane-copper-catalyzed asymmetric conjugate addition of dialkylzinc. Tetrahedron 2007, 63, 6573. <http://dx.doi.org/10.1016/j.tet.2007.03.032>
  • Chen Qian, Kuriyama Masami, Soeta Takahiro, Hao Xinyu, Yamada Ken-ichi, Tomioka Kiyoshi: Asymmetric Synthesis of 5-Arylcyclohexenones by Rhodium(I)-Catalyzed Conjugate Arylation of Racemic 5-(Trimethylsilyl)cyclohexenone with Arylboronic Acids. Org Lett 2005, 7, 4439. <http://dx.doi.org/10.1021/ol051704m>
  • Fujimura Takashi, Nakashima Hiromi, Sakagami Hideki, Taniguchi Takahiko, Ogasawara Kunio: Diastereocontrolled synthesis of an enantiopure 4,4-disubstituted cyclohex-2-en-ol: a new route to (+)-quebrachamine. Tetrahetron Lett 2002, 43, 97. <http://dx.doi.org/10.1016/S0040-4039(01)02075-5>
  • Lange Gordon L., Humber Craig C., Manthorpe Jeffrey M.: [2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons. Tet Asymm 2002, 13, 1355. <http://dx.doi.org/10.1016/S0957-4166(02)00339-7>
  • Ramesh Namakkal G, Bakkeren Frank J.A.D, Groot Debby de, Passamonti Umberto, Klunder Antonius J.H, Zwanenburg Binne: Asymmetric desymmetrization of pseudo-meso 5-hydroxy-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-ones. Tetrahedron 2001, 57, 9877. <http://dx.doi.org/10.1016/S0040-4020(01)01007-9>
  • Tanaka Keigo, Taniguchi Takahiko, Ogasawara Kunio: 7,7-Dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of ketodicyclopentadiene: a new route to (−)-physostigmine, (−)-physovenine, and (−)-aphanorphine. Tetrahetron Lett 2001, 42, 1049. <http://dx.doi.org/10.1016/S0040-4039(00)02171-7>
  • Mehta Goverdhan, Reddy D.Srinivasa: Enzymatic resolution of dioxygenated dicyclopentadienes: Enantiopure hydrindanes, hydroisoquinolones, diquinanes and application to a synthesis of (+)-coronafacic acid. Tetrahetron Lett 1999, 40, 991. <http://dx.doi.org/10.1016/S0040-4039(98)02465-4>
  • Iura Yosuke, Sugahara Tsutomu, Ogasawara Kunio: Oxidative resolution of 2-cyclopentenols by the asymmetric hydrogen transfer protocol. Tetrahetron Lett 1999, 40, 5735. <http://dx.doi.org/10.1016/S0040-4039(99)01087-4>
  • Hareau-Vittini Georges, Hikichi Shinichi, Sato Fumie: Eine überraschendecis-selektive 1,4-Addition von Cyanocupraten niedriger Ordnung an optisch aktives 5-(tert-Butyldimethylsilyloxy)-2-cyclohexenon. Angew Chem 1998, 110, 2221. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980803)110:15<2221::AID-ANGE2221>3.0.CO;2-U>
  • Jiang Shende, Singh Gurdial: Chemical synthesis of shikimic acid and its analogues. Tetrahedron 1998, 54, 4697. <http://dx.doi.org/10.1016/S0040-4020(98)00016-7>
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  • Sato Fumie, Hikichi Shinichi, Hareau Georges P-J.: Efficient and practical synthesis of optically active 5-t-butyldimethylsiloxy-2-cyclohexenone as a convenient chiral 2,5-cyclohexadienone synthon. Tetrahetron Lett 1997, 38, 8299. <http://dx.doi.org/10.1016/S0040-4039(97)10206-4>
  • Shimizu Masahiro, Kamikubo Takashi, Ogasawara Kunio: A new enantiocontrolled synthesis of (−)-(R)-mevalonolactone. Tet Asymm 1997, 8, 2519. <http://dx.doi.org/10.1016/S0957-4166(97)00299-1>
  • Zhu J., Klunder A. J. H., Smits J. M. M., Beurskens Paul T., Beurskens Gezina: Crystal and molecular structure of heptacyclo [9,6,1,14,7,114,17,02,10,03,8,01,13]-eicosa-3(8),5,12,15-tetrene-9, 18-dione. J Chem Crystallogr 1996, 26, 559. <http://dx.doi.org/10.1007/BF01668415>
  • Sugahara Tsutomu, Ogasawara Kunio: Contra-steric Diels-Alder route to 3-oxodicyclopentadiene and meso 3,5-endo-dihydroxy-4,5-dihydrodicyclopentadiene. Tetrahetron Lett 1996, 37, 205. <http://dx.doi.org/10.1016/0040-4039(95)02129-9>
  • Kamikubo Takashi, Hiroya Kou, Ogasawara Kunio: Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (−)-phyllostine, via catalytic asymmetrization of a meso substrate. Tetrahetron Lett 1996, 37, 499. <http://dx.doi.org/10.1016/0040-4039(95)02190-6>
  • Bakkeren Frank J.A.D., Remesh Namakkal G., de Groot Debby, Klunder Antonius J.H., Zwanenburg Binne: Asymmetric desymmetrization of a Pseudo-mesoendo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one by chiral amines. Tetrahetron Lett 1996, 37, 8003. <http://dx.doi.org/10.1016/0040-4039(96)01810-2>
  • Schoffers Elke, Golebiowski Adam, Johnson Carl R.: Enantioselective synthesis through enzymatic asymmetrization. Tetrahedron 1996, 52, 3769. <http://dx.doi.org/10.1016/S0040-4020(95)01021-1>
  • Hiroya Kou, Kurihara Yuko, Ogasawara Kunio: Asymmetrische katalytische Isomerisierung vonmeso-1,4-Endiolethern mit einem chiralen binap-RhI-Komplex. Angew Chem 1995, 107, 2445. <http://dx.doi.org/10.1002/ange.19951072022>
  • Zhu Jie, Yang Ji-Ying, Klunder Antonius J.H, Liu Zhi-Yu, Zwanenburg Binne: A stereo- and enantioselective approach to clavulones from tricyclodecadienone using flash vacuum thermolysis. Tetrahedron 1995, 51, 5847. <http://dx.doi.org/10.1016/0040-4020(95)00237-3>
  • Zhu Jie, van der Hoeven John: Facial stereoselectivity in lithium dialkylcuprate additions to functionalized endo-Tricyclo[5.2.1.02,6]decadienones. Tetrahedron 1995, 51, 10953. <http://dx.doi.org/10.1016/0040-4020(95)00651-N>
  • Zhu Jie, Klunder Antonius J.H, Zwanenburg Binne: Synthesis of 6-functionalized tricyclodecadienones using Barton's radical decarboxylation reaction. Generation of tricyclo[5.2.1.02,6]decatrienone, a norbornene annulated cyclopentadienone. Tetrahedron 1995, 51, 5099. <http://dx.doi.org/10.1016/0040-4020(95)98707-O>
  • Zhu Jie, Klunder Antonius J.H, Zwanenburg Binne: A facile approach to norbornene-annulated cyclopentenones, a novel class of tricyclodecadienones. Tetrahedron 1995, 51, 5117. <http://dx.doi.org/10.1016/0040-4020(95)98708-P>
  • Kamikubo Takashi, Ogasawara Kunio: The enantiodivergent total synthesis of natural and unnatural enantiomers of theobroxide. Tetrahetron Lett 1995, 36, 1685. <http://dx.doi.org/10.1016/0040-4039(95)00131-U>