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Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 667-676

http://dx.doi.org/10.1351/pac200779040667

Progress toward a total synthesis of spirastrellolide A

Ian Paterson, Edward A. Anderson, Stephen M. Dalby, Jong Ho Lim, Olivier Loiseleur, Philip Maltas and Christian Moessner

University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK

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  • Kobayashi Shū, Endo Toshimitsu, Yoshino Takumi, Schneider Uwe, Ueno Masaharu: Allylation Reactions of Aldehydes with Allylboronates in Aqueous Media: Unique Reactivity and Selectivity that are Only Observed in the Presence of Water. Chem. Asian J. 2013, 8, 2033. <http://dx.doi.org/10.1002/asia.201300440>
  • Wang Chao-Chao, Tang Yu, Yang Ka, Li Xiao-Yu, Wu Yi-Biao, Hsung Richard P.: A carbohydrate based chiron approach to the lactone intermediate employed in the synthesis of BC-ring fragment of (+)-spirastrellolide A. Tetrahedron 2013, 69, 8284. <http://dx.doi.org/10.1016/j.tet.2013.07.009>
  • Lorente Adriana, Lamariano-Merketegi Janire, Albericio Fernando, Álvarez Mercedes: Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea. Chem. Rev. 2013, 113, 4567. <http://dx.doi.org/10.1021/cr3004778>
  • Sabitha Gowravaram, Rao Allu Senkara, Yadav J. S.: Synthesis of the C1–C25 southern domain of spirastrellolides B and F. Org. Biomol. Chem. 2013, 11, 7218. <http://dx.doi.org/10.1039/c3ob41345d>
  • Paterson Ian, Maltas Philip, Anderson Edward A.: Total synthesis of (+)-spirastrellolide A methyl ester: Challenges and discoveries. Pure Appl. Chem. 2013, 1. <http://dx.doi.org/10.1351/PAC-CON-13-01-01>
  • Paterson Ian, Maltas Philip, Dalby Stephen M., Lim Jong Ho, Anderson Edward A.: A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester. angew chemie 2012, 124, 2803. <http://dx.doi.org/10.1002/ange.201108594>
  • Paterson Ian, Maltas Philip, Dalby Stephen M., Lim Jong Ho, Anderson Edward A.: A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester. Angew Chem Int E 2012, 51, 2749. <http://dx.doi.org/10.1002/anie.201108594>
  • Paterson Ian, Anderson Edward A., Dalby Stephen M., Lim Jong Ho, Maltas Philip, Loiseleur Olivier, Genovino Julien, Moessner Christian: The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments. Org. Biomol. Chem. 2012, 10, 5861. <http://dx.doi.org/10.1039/c2ob25100k>
  • Paterson Ian, Anderson Edward A., Dalby Stephen M., Lim Jong Ho, Maltas Philip: The stereocontrolled total synthesis of spirastrellolide A methyl ester. Fragment coupling studies and completion of the synthesis. Org. Biomol. Chem. 2012, 10, 5873. <http://dx.doi.org/10.1039/c2ob25101a>
  • P. Hsung Richard, Tang Yu, Yang Jin-Haek, Liu Jia, Wang Chao-Chao, Lv Ming-Can, Wu Yi-Biao, Yu Xue-Liang, Ko Changhong: ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL. HETEROCYCLES 2012, 86, 565. <http://dx.doi.org/10.3987/COM-12-S(N)54>
  • Kobayashi Shū, Endo Toshimitsu, Ueno Masaharu: Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes. angew chemie 2011, 123, 12470. <http://dx.doi.org/10.1002/ange.201106433>
  • Kobayashi Shū, Endo Toshimitsu, Ueno Masaharu: Chiral Zinc-Catalyzed Asymmetric α-Alkylallylation and α-Chloroallylation of Aldehydes. Angew Chem Int E 2011, 50, 12262. <http://dx.doi.org/10.1002/anie.201106433>
  • Paterson Ian, Dalby Stephen M., Maltas Philip: Strategy Evolution in the Total Synthesis of Spirastrellolide A Methyl Ester. Isr J Chem 2011, 51, 406. <http://dx.doi.org/10.1002/ijch.201100007>
  • Smith Amos B., Smits Helmars, Kim Dae-Shik: Spirastrellolide studies. Synthesis of the C(1)–C(25) southern hemispheres of spirastrellolides A and B, exploiting anion relay chemistry. Tetrahedron 2010, 66, 6597. <http://dx.doi.org/10.1016/j.tet.2010.01.082>
  • Paterson Ian, Dalby Stephen M.: Synthesis and stereochemical determination of the spirastrellolides. Nat Prod Rep 2009, 26, 865. <http://dx.doi.org/10.1039/b906991g>
  • Paterson Ian, Anderson Edward A., Dalby Stephen M., Lim Jong Ho, Genovino Julien, Maltas Philip, Moessner Christian: Total Synthesis of Spirastrellolide A Methyl Ester—Part 1: Synthesis of an Advanced C17–C40 Bis-spiroacetal Subunit. Angew Chem 2008, 120, 3058. <http://dx.doi.org/10.1002/ange.200705565>
  • Paterson Ian, Anderson Edward A., Dalby Stephen M., Lim Jong Ho, Genovino Julien, Maltas Philip, Moessner Christian: Total Synthesis of Spirastrellolide A Methyl Ester—Part 1: Synthesis of an Advanced C17–C40 Bis-spiroacetal Subunit. Angew Chem Int Ed 2008, 47, 3016. <http://dx.doi.org/10.1002/anie.200705565>
  • Paterson Ian, Anderson Edward A., Findlay Alison D., Knappy Christopher S.: Total synthesis of pteridic acids A and B. Tetrahedron 2008, 64, 4768. <http://dx.doi.org/10.1016/j.tet.2008.01.132>
  • Paterson Ian, Anderson Edward A., Dalby Stephen M., Lim Jong Ho, Loiseleur Olivier, Maltas Philip, Moessner Christian: Progress Toward a Total Synthesis of Spirastrellolide A. ChemInform 2007, 38. <http://dx.doi.org/10.1002/chin.200738251>