Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds

References (63)

1. 1 Wiest, O., and Houk, K.N. (1996). Density Functional Theory IV, Springer. [1st ed.].
2. 2 Marvell, E.N. (1980). Thermal Electrocyclic Reactions, Academic Press.
3. 3 Ansari, F.L., Qureshi, R., and Qureshi, M.L. (1999). Electrocyclic Reactions, Wiley-VCH.
4. 4 Nicolaou, 2002, The Diels–Alder Reaction in Total Synthesis [DOI]
5. 5 Jones, 2014, Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements [DOI]
6. 6 Beaudry, 2005, Biosynthetic and Biomimetic Electrocyclizations [DOI]
7. 7 Bian, 2017, Recent Advances on the Application of Electrocyclic Reactions in Complex Natural Product Synthe-sis [DOI]
8. 8 Sheikh, 2015, 4π electrocyclisation in domino processes: Contemporary trends and synthetic applications towards natural products [DOI]
9. 9 Vargas, 2018, The 6π-azaelectrocyclization of azatrienes. Synthetic applications in natural products, bioactive heterocycles, and related fields [DOI]
10. 10 Derewacz, 2015, Mapping Microbial Response Metabolomes for Induced Natural Product Discovery [DOI]
11. 11 Nicolaou, 2000, Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans [DOI]
12. 12 Tejedor, D., Delgado-Hernández, S., Diana-Rivero, R., Díaz-Díaz, A., and García-Tellado, F. (2019). Recent Advances in the Synthesis of 2H-Pyrans. Molecules, 24. [DOI]
13. 13 Bishop, 2008, Mechanistic Investigations of the Acid-Catalyzed Cyclization of a Vinyl ortho-Quinone Methide [DOI]
14. 14 Krasnaya, 1999, Dienone ⇄ 2H-pyran valence isomerization [DOI]
15. 15 Tsuda, 1988, Nickel(0)-catalyzed reaction of diynes with aldehydes [DOI]
16. 16 Lillya, 1971, Molecular spectra and conformations of conjugated dienones [DOI]
17. 17 Gosink, 1974, Valence isomers. Substituent effects on the equilibrium between 2H-pyrans and cis-dienones [DOI]
18. 18 Peng, 2011, Substituent-Controlled Electrocyclization of 2,4-Dienones: Synthesis of 2,3,6-Trisubstituted 2H-Pyran-5-carboxylates and Their Transformations [DOI]
19. 19 Menz, 2006, Synthesis of Stable 2H-Pyran-5-carboxylates via a Catalyzed Propargyl-Claisen Rearrangement/Oxa-6π Electrocyclization Strategy [DOI]
20. 20 Tejedor, 2017, Integrative Pericyclic Cascade: An Atom Economic, Multi C−C Bond-Forming Strategy for the Construction of Molecular Complexity [DOI]
21. 21 Bankura, 2020, C 3 -Thioester/-Ester Substituted Linear Dienones: A Pluripotent Molecular Platform for Diversification via Cascade Pericyclic Reactions [DOI]
22. 22 Lee, 1996, Torreyanic Acid: A Selectively Cytotoxic Quinone Dimer from the Endophytic Fungus Pestalotiopsis microspora [DOI]
23. 23 Li, 2000, Total Synthesis of (±)-Torreyanic Acid [DOI]
24. 24 Li, 2003, Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid: Application of a Biomimetic Oxidation/Electrocyclization/Diels−Alder Dimerization Cascade1 [DOI]
25. 25 Bellavance, 2018, Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocy-clization [DOI]
26. 26 Shoji, 2005, Total Synthesis of Epoxyquinols A, B, and C and Epoxytwinol A and the Reactivity of a 2H-Pyran Derivative as the Diene Component in the Diels−Alder Reaction [DOI]
27. 27 Shen, 2003, A Formal [3 + 3] Cycloaddi-tion Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Elec-trocyclic Ring Closure of 1-Oxatrienes [DOI]
28. 28 Richard, 2005, A Formal [3 + 3] Cycloaddition Approach to Natural-Product Synthesis [DOI]
29. 29 Sunazuka, 2002, The First Total Synthesis of (±)-Arisugacin A, a Potent, Orally Bioavailable Inhibitor of Acetylcholinesterase [DOI]
30. 30 Zehnder, 2000, A Concise Stereoselective Route to the Pentacyclic Frameworks of Arisugacin A and Territrem B [DOI]
31. 31 Cole, 2002, The first enantioselective total synthesis of (−)-arisugacin A [DOI]
32. 32 Malerich, 2003, Biomimetic Synthesis of (±)-Pinnatal and (±)-Sterekunthal A [DOI]
33. 33 Tang, 2009, Total Synthesis of Phomactin A [DOI]
34. 34 Buchanan, 2011, Total Synthesis of (±)-Phomactin A. Lessons Learned from Respecting a Challenging Structural Topology [DOI]
35. 35 Kang, 2003, Total Synthesis of the Highly Potent Anti-HIV Natural Product Daurichromenic Acid along with Its Two Chromane Derivatives, Rhododaurichromanic Acids A and B [DOI]
36. 36 Kurdyumov, 2003, Formal [3 + 3] Cycloaddition Approach to Chromenes and Chromanes. Concise Total Syntheses of (±)-Rhododaurichromanic Acids A and B and Methyl (±)-Daurichromenic Ester [DOI]
37. 37 Tisdale, 2003, Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels–Alder/Claisen rearrangement [DOI]
38. 38 Jung, 2010, Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products [DOI]
39. 39 Jacob, 2014, No Acid Required: 4π and 6π Electrocyclization Reactions of Dienyl Diketones for the Synthesis of Cyclopentenones and 2H-Pyrans [DOI]
40. 40 Yamashita, 2008, A Concise Synthesis of the Pentacyclic Framework of Cortistatins [DOI]
41. 41 Yamashita, 2011, Total Synthesis of Cortistatins A and J [DOI]
42. 42 Holla, 2012, Synthesis of melicodenines C, D and E [DOI]
43. 43 Schwan, 2020, Five-Step Synthesis of Yaequinolones J1 and J2 [DOI]
44. 44 Zhang, 2020, Concise Biosynthesis of Phenylfuropyridones in Fungi [DOI]
45. 45 Fotiadou, 2012, Electrocyclization of Oxatrienes in the Construction of Structurally Complex Pyranopyridones [DOI]
46. 46 Wang, 2007, Efficient Synthesis of Substituted Pyranoquinolinones from 2,4-Dihydroxyquinoline: Total Synthesis of Zanthosimuline, cis-3′,4′-Dihydroxy-3′,4′-Dihydroflindersine, and Orixalone D [DOI]
47. 47 Thompson, 2011, Asymmetric electrocyclic reactions [DOI]
48. 48 Kobayashi, 2019, Asymmetric Synthesis and Structure Revision of Guignardone H and I: Development of a Chiral 1,3-Diketone Possessing C2 Symmetry [DOI]
49. 49 Kobayashi, 2020, Sequential condensation-6π-electrocyclization reaction of a chiral 1,3-Diketone possessing C2 symmetry [DOI]
50. 50 Yan, 2020, Asymmetric Total Synthesis of (−)-Guignardones A and B [DOI]
51. 51 Murray, 2019, Total Synthesis of Naphterpin and Marinone Natural Products [DOI]
52. 52 Tambar, 2005, Progress toward the Total Synthesis of Saudin: Development of a Tandem Stille-Oxa-Electrocyclization Reaction [DOI]
53. 53 Tambar, 2006, Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin [DOI]
54. 54 Tambar, 2007, The development and scope of a versatile tandem Stille-oxa-electrocyclization reaction [DOI]
55. 55 Parker, 2011, Convergent synthesis of 2H-chromenes—a formal [3+3] cycloaddition by a one-pot, three-step cascade [DOI]
56. 56 Uyanik, 2020, Chemoselective oxidative generation of ortho-quinone methides and tandem transformations [DOI]
57. 57 Iguchi, 2016, Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight [DOI]
58. 58 Cole, 2003, Intramolecular Formal oxa-[3 + 3] Cycloaddition Approach to the ABD System of Phomactin A [DOI]
59. 59 Olson, 2005, Concise Synthesis of (±)-Smenochromene D (= Likonide B)
60. 60 Hall, 2017, Synthesis of Briarane Diterpenoids: Biomimetic Transannular Oxa-6π electrocyclization Induced by a UVA/UVC Photoswitch [DOI]
61. 61 Kutateladze, 2019, Reassignments and Corroborations of Oxo-Bridged Natural Products Di-rected by OSE and DU8+ NMR Computation [DOI]
62. 62 Boon, 2017, Using Ring Strain to Control 4π-Electrocyclization Reactions: Torquoselectivity in Ring Closing of Medium-Ring Dienes and Ring Opening of Bicyclic Cyclobutenes [DOI]
63. 63 Si, 2019, Insight into 6π Electrocyclic Reactions of 1,8-Dioxatetraene [DOI]

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