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[3.3] Sigmatropy within 1-vinyl-2-alkenyl-7,7-dimethyl-exo-norbornan-2-ols. The first atropselective oxyanionic Cope rearrangement

Cite this: J. Am. Chem. Soc. 1990, 112, 1, 277–283
Publication Date (Print):January 1, 1990
https://doi.org/10.1021/ja00157a043
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  2. Paul D. Thornton and, D. Jean Burnell. A Pauson−Khand and Ring-Expansion Approach to the Aquariane Ring System. Organic Letters 2006, 8 (15) , 3195-3198. https://doi.org/10.1021/ol0609715
  3. Leo A. Paquette and, John E. Hofferberth. Effect of 9,10-Cyclic Acetal Stereochemistry on Feasible Operation of the α-Ketol Rearrangement in Highly Functionalized Paclitaxel (Taxol) Precursors. The Journal of Organic Chemistry 2003, 68 (6) , 2266-2275. https://doi.org/10.1021/jo020627v
  4. Jiong Yang,, Yun Oliver Long, and, Leo A. Paquette. Concise Total Syntheses of the Bioactive Mesotricyclic Diterpenoids Jatrophatrione and Citlalitrione. Journal of the American Chemical Society 2003, 125 (6) , 1567-1574. https://doi.org/10.1021/ja021177r
  5. Leo A. Paquette,, Y. Ravindra Reddy,, Grigoriy Vayner, and, K. N. Houk. High-Rate Accelerations in Oxy-Cope Rearrangements Induced by Sulfur Substitution:  Kinetic Study Involving Electronically and Geometrically Differentiated 1-Alkenyl-2-(Z-1-propenyl)-7,7-dimethyl-exo-norbornan-2-ols. Journal of the American Chemical Society 2000, 122 (44) , 10788-10794. https://doi.org/10.1021/ja0025402
  6. Jeffrey M. Warrington,, Glenn P. A. Yap, and, Louis Barriault. Tandem Oxy-Cope/Transannular Ene Reaction of 1,2-Divinylcyclohexanols. Organic Letters 2000, 2 (5) , 663-665. https://doi.org/10.1021/ol005502w
  7. Leo A. Paquette,, Y. Ravindra Reddy,, Fredrik Haeffner, and, K. N. Houk. Consequences of Heteroatomic C-6 Substitution on Rates of the Oxyanionic Cope Rearrangement. The Remarkable Accelerating Effect of Sulfide Groups. Journal of the American Chemical Society 2000, 122 (4) , 740-741. https://doi.org/10.1021/ja993725f
  8. Hon-Chung Tsui and, Leo A. Paquette. Reversible Charge-Accelerated Oxy-Cope Rearrangements. The Journal of Organic Chemistry 1998, 63 (26) , 9968-9977. https://doi.org/10.1021/jo982002w
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  10. Leo A. Paquette,, Hui-Ling Wang,, Qingbei Zeng, and, Tzenge-Lien Shih. Heteroatomic Modulation of Oxyanionic Cope Rearrangement Rates. Consequences on Competing Nucleophilic Cleavage of an Oxetane Ring in Precursors to Paclitaxel. The Journal of Organic Chemistry 1998, 63 (19) , 6432-6433. https://doi.org/10.1021/jo981059f
  11. Leo A. Paquette and, Mangzhu Zhao. Enantiospecific Total Synthesis of Natural (+)-Taxusin. 1. Retrosynthesis, Advancement to Diastereomeric trans-Δ9,10-Tricyclic Olefinic Intermediates, and the Stereocontrol Attainable Because of Intrinsic Rotational Barriers Therein. Journal of the American Chemical Society 1998, 120 (21) , 5203-5212. https://doi.org/10.1021/ja9805371
  12. Leo A. Paquette,, Li-Qiang Sun,, Timothy J. N. Watson,, Dirk Friedrich, and, Brett T. Freeman. Utilization of the Phenylthio Substituent as a Multipurpose Synthetic Tool. Direct Application to the Enantioselective Construction of (−)-Salsolene Oxide. The Journal of Organic Chemistry 1997, 62 (23) , 8155-8161. https://doi.org/10.1021/jo971244d
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  14. Xian-Lei Wang, Yun-Yu Lu, Jie Wang, Xuan Wang, He-Quan Yao, Guo-Qiang Lin, Bing-Feng Sun. A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol. Org. Biomol. Chem. 2014, 12 (22) , 3562-3566. https://doi.org/10.1039/C4OB00046C
  15. Ángel M. Montaña, Stefano Ponzano, Consuelo Batalla, Mercè Font-Bardia. Unprecedented double benzylic rearrangement: regio- and stereospecific tandem 1,4-shift and Curtin rearrangement. Tetrahedron 2012, 68 (39) , 8276-8285. https://doi.org/10.1016/j.tet.2012.07.053
  16. David R. Armstrong, David V. Graham, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara. A Structural and Computational Study of Synthetically Important Alkali-Metal/Tetramethylpiperidide (TMP) Amine Solvates. Chemistry - A European Journal 2008, 14 (26) , 8025-8034. https://doi.org/10.1002/chem.200800158
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  19. Mauricio Gomes Constantino, Kleber Thiago de Oliveira, Adilson Beatriz, Gil Valdo José da Silva. A synthetic approach to bicyclo[6.2.1]undecane ring systems. Tetrahedron Letters 2003, 44 (13) , 2641-2643. https://doi.org/10.1016/S0040-4039(03)00377-0
  20. Leo Paquette, Qingbei Zeng, Hui-Ling Wang, Tzenge-Lien Shih. From Carbohydrates to the Discovery of Pronounced Heteroatomic Effects on Anionically Accelerated [3,3]-Sigmatropic Rearrangements. European Journal of Organic Chemistry 2000, 2000 (12) , 2187-2194. https://doi.org/10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187>3.0.CO;2-2
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  24. Timo V. Ovaska, Jayme L. Roark, Christina M. Shoemaker, Jon Bordner. A convenient route to fused 5-7-6 tricyclic ring systems. Tetrahedron Letters 1998, 39 (32) , 5705-5708. https://doi.org/10.1016/S0040-4039(98)01198-8
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  28. Julia M. Dickinson. Ions, Radicals, Carbenes and Other Monocoordinated Systems. 1995,,, 1087-1145. https://doi.org/10.1016/B0-08-044705-8/00233-8
  29. . References to Volume 1. 1995,,, 1147-1316. https://doi.org/10.1016/B0-08-044705-8/09009-9
  30. Olivier Riant, Henri B. Kagan, Louis Ricard. Asymmetric base-catalyzed cycloaddition between anthrone and some dienophiles. Tetrahedron 1994, 50 (15) , 4543-4554. https://doi.org/10.1016/S0040-4020(01)89385-6
  31. Kyriacos Costa Nicolaou, Wei-Min Dai, Rodney Kiplin Guy. Chemistry and Biology of Taxol. Angewandte Chemie International Edition in English 1994, 33 (1) , 15-44. https://doi.org/10.1002/anie.199400151
  32. Kyriacos Costa Nicolaou, Wei-Min Dai, Rodney Kiplin Guy. Chemie und Biologie von Taxol. Angewandte Chemie 1994, 106 (1) , 38-69. https://doi.org/10.1002/ange.19941060105
  33. Darren M. Heaton, Keith D. Bartle, Christopher M. Rayner, Anthony A. Clifford. Application of supercritical fluid extraction and supercritical fluid chromatography to the production of taxanes as anti-cancer drugs. Journal of High Resolution Chromatography 1993, 16 (11) , 666-670. https://doi.org/10.1002/jhrc.1240161109
  34. Charles S. Swindell. Chemical Studies of the Taxane Diterpenes. 1993,,, 179-231. https://doi.org/10.1016/B978-0-444-89366-6.70012-5
  35. Leo A. Paquette, Mangzhu Zhao, Dirk Friedrich. An unprecedented silyl triflate-promoted hydride shift within a taxane derivative. Tetrahedron Letters 1992, 33 (48) , 7311-7314. https://doi.org/10.1016/S0040-4039(00)60174-0
  36. Leo A. Paquette, Steven W. Elmore, Keith D. Combrink, Eugene R. Hickey, Robin D. Rogers. An Enantioselective Approach to the Taxanes: Direct access to functionalizedcis-tricyclo[9.3.1.03,8]pentadecanesvia ?-hydroxy ketone andWagner-Meerwein rearrangements. Helvetica Chimica Acta 1992, 75 (6) , 1755-1771. https://doi.org/10.1002/hlca.19920750603
  37. Leo A. Paquette, Keith D. Combrink, Steven W. Elmore, Mangzhu Zhao. Setting the Bridgehead Oxidation Level intrans-Tricyclo[9.3.1.03,8]pentadecanes as a Prelude to the Dual Synthesis of Taxol and Taxusin. Helvetica Chimica Acta 1992, 75 (6) , 1772-1791. https://doi.org/10.1002/hlca.19920750604
  38. Randy W. Jackson, Richard G. Higby, Kenneth J. Shea. Stereoselective elaboration of the tricyclo[9.3.1.03,8]pentadecane ring system. Atropisomeric control of stereochemistry. Tetrahedron Letters 1992, 33 (33) , 4695-4698. https://doi.org/10.1016/S0040-4039(00)61261-3
  39. Stephen A. Hitchcock, Gerald Pattenden. A tandem radical macrocyclisation - radical transannulation strategy to the taxane ring system. Tetrahedron Letters 1992, 33 (33) , 4843-4846. https://doi.org/10.1016/S0040-4039(00)61300-X
  40. Nicos A. Petasis, Michael A. Patane. The synthesis of carbocyclic eight-membered rings. Tetrahedron 1992, 48 (28) , 5757-5821. https://doi.org/10.1016/S0040-4020(01)90172-3
  41. G. Mehta, R. Barone, P. Azario, F. Barberis, M. Arbelot, M. Chanon. New computer-based approach for seeking a key step in the synthesis of complex structures. Application to Taxane and Crinipellin Diterpenoid Frameworks.. Tetrahedron 1992, 48 (41) , 8953-8962. https://doi.org/10.1016/S0040-4020(01)81994-3
  42. Randy W. Jackson, Richard G. Higby, Jeffrey W. Gilman, Kenneth J. Shea. The chemistry of C-aromatic taxane derivatives atropisomer control of reaction stereochemistry. Tetrahedron 1992, 48 (34) , 7013-7032. https://doi.org/10.1016/S0040-4020(01)91211-6
  43. Steven W. Elmore, Keith D. Combrink, Leo A. Paquette. A convenient means for controlling the oxidation level of bridgehead carbon C-1 in functionalized tricyclo[9.3.1.03,8]pentadecanes. Tetrahedron Letters 1991, 32 (46) , 6679-6682. https://doi.org/10.1016/S0040-4039(00)93573-1
  44. Tsuneo Imamoto. Organocerium Reagents. 1991,,, 231-250. https://doi.org/10.1016/B978-0-08-052349-1.00008-1
  45. Steven W. Elmore, Leo A. Paquette. The first thermally-induced retro-oxy-cope rearrangement. Tetrahedron Letters 1991, 32 (3) , 319-322. https://doi.org/10.1016/S0040-4039(00)92617-0
  46. Katsuhiko Tomooka, Shih-Yi Wei, Takeshi Nakai. Acyclic Oxy-Cope Rearrangement. Dependence of E / Z Stereoselection on Substrate Stereochemistry. Chemistry Letters 1991, 20 (1) , 43-46. https://doi.org/10.1246/cl.1991.43
  47. Leo A. Paquette. Stereokontrollierte Synthese komplizierter cyclischer Ketone durch Oxy-Cope-Umlagerung. Angewandte Chemie 1990, 102 (6) , 642-660. https://doi.org/10.1002/ange.19901020606
  48. L. A. PAQUETTE, N. A. PEGG, D. TOOPS, G. D. MAYNARD, R. D. ROGERS. ChemInform Abstract: (3.3) Sigmatropy Within 1-Vinyl-2-alkenyl-7,7-dimethyl-exo-norbornan-2-ols. The First Atropselective Oxyanionic Cope Rearrangement.. ChemInform 1990, 21 (15) https://doi.org/10.1002/chin.199015059

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