Total Synthesis of (–)‐Heliespirone A and (+)‐Heliespirone C
作者： Philip Norcott , Christopher S. P. McErlean
关键词: Sigmatropic reaction 、 Claisen rearrangement 、 Enantioselective synthesis 、 Total synthesis 、 Sharpless asymmetric dihydroxylation 、 Michael reaction 、 Carroll rearrangement 、 Intramolecular force 、 Stereochemistry 、 Chemistry
摘要: Total syntheses of the spiro-epimeric natural products (–)-heliespirone A and (+)-heliespirone C are described. The successful strategy involved an aromatic Claisen rearrangement, a diastereoselective Sharpless asymmetric dihydroxylation (AD) reaction, intramolecular oxa-Michael addition.
sci-hub.se 参考文章(39)
Christopher J. Moody, Claisen rearrangements in heteroaromatic systems Advances in Heterocyclic Chemistry. ,vol. 42, pp. 203- 244 ,(1987) , 10.1016/S0065-2725(08)60644-3
Francisco A. Macías, Rosa.M. Varela, Ascensión Torres, JoséMa G. Molinillo, Heliespirone A. The first member of a novel family of bioactive sesquiterpenes Tetrahedron Letters. ,vol. 39, pp. 427- 430 ,(1998) , 10.1016/S0040-4039(97)10538-X
Christopher S. P. McErlean, Christopher J. Moody, First synthesis of N-(3-carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an unusual quinone isolated from Embelia ribes. Journal of Organic Chemistry. ,vol. 72, pp. 10298- 10301 ,(2007) , 10.1021/JO702101W
FA Macias, FR Fronczek, None, The absolute configuration of heliespirone B, from sunflower Helianthus annuus Acta Crystallographica Section E-structure Reports Online. ,vol. 63, ,(2007) , 10.1107/S160053680701478X
Suciati, James A. Fraser, Lynette K. Lambert, Gregory K. Pierens, Paul V. Bernhardt, Mary J. Garson, Secondary metabolites of the sponge-derived fungus Acremonium persicinum Journal of Natural Products. ,vol. 76, pp. 1432- 1440 ,(2013) , 10.1021/NP4002114
Ana M. Martín Castro, Claisen rearrangement over the past nine decades. Chemical Reviews. ,vol. 104, pp. 2939- 3002 ,(2004) , 10.1021/CR020703U
Akari Miyawaki, Daisuke Kikuchi, Masu Niki, Yuki Manabe, Makoto Kanematsu, Hiromasa Yokoe, Masahiro Yoshida, Kozo Shishido, Total synthesis of natural enantiomers of heliespirones A and C via the diastereoselective intramolecular Hosomi-Sakurai reaction. Journal of Organic Chemistry. ,vol. 77, pp. 8231- 8243 ,(2012) , 10.1021/JO3016055
David R. Appleton, Cheah Shiau Chuen, Michael V. Berridge, Victoria L. Webb, Brent R. Copp, Rossinones A and B, biologically active meroterpenoids from the Antarctic ascidian, Aplidium species. Journal of Organic Chemistry. ,vol. 74, pp. 9195- 9198 ,(2009) , 10.1021/JO901846J
Philip Norcott, Calan Spielman, Christopher S. P. McErlean, An in-water, on-water domino process for synthesis Green Chemistry. ,vol. 14, pp. 605- 609 ,(2012) , 10.1039/C2GC16259H
Gregory B. BENNETT, The Claisen Rearrangement in Organic Synthesis; 1967 to January 1977 Synthesis. ,vol. 1977, pp. 589- 606 ,(1977) , 10.1055/S-1977-24491