Organic Synthesis

Contents Preface Organic Functional Group Interconversion and Protection 1. Functional Group Transformations http://www.organic-chemistry.org/Highlights/2012/14May.shtm May 14, 2012 2. Functional Group Interconversion http://www.organic-chemistry.org/Highlights/2012/22October. shtm October 22, 2012 3. Functional Group Interconversion http://www.organic-chemistry.org/Highlights/2013/13May.shtm May 13, 2013 4. Functional Group Interconversion http://www.organic-chemistry.org/Highlights/2013/28October. shtm October 28, 2013 5. Reduction and Oxidation http://www.organic-chemistry.org/Highlights/2012/21May.shtm May 21, 2012 6. Functional Group Oxidation and Reduction http://www.organic-chemistry.org/Highlights/2012/12November .shtm November 12, 2012 7. Functional Group Oxidation http://www.organic-chemistry.org/Highlights/2013/20May.shtm May 20, 2013 8. Functional Group Reduction http://www.organic-chemistry.org/Highlights/2013/27May.shtm May 27, 2013 9. Functional Group Protection http://www.organic-chemistry.org/Highlights/2012/28May.shtm May 28, 2012 10. Functional Group Protection http://www.organic-chemistry.org/Highlights/2012/29October. shtm October 29, 2012 11. Functional Group Protection http://www.organic-chemistry.org/Highlights/2013/10June.sht m June 12, 2013 12. Functional Group Protection http://www.organic-chemistry.org/Highlights/2013/11November .shtm November 11, 2013 Flow Methods 13. Develop of Flow Reactions September 24, 2012 14. Flow Chemistry http://www.organic-chemistry.org/Highlights/2013/25March.sh tm March 25, 2013 15. Flow Chemistry http://www.organic-chemistry.org/Highlights/2013/30Septembe r.shtm September 30, 2013 C-H Functionalization 16. C-H Functionalization: The Ono/Kato/Dairi Synthesis of Fusiocca-1,10(14)-diene-3,8?,16-triol http://www.organic-chemistry.org/Highlights/2012/19March.sh tm March 19, 2012 17. C-H Functionalization http://www.organic-chemistry.org/Highlights/2012/17Septembe r.shtm September 17, 2012 18. C-H Functionalization: The Hatakeyama Synthesis of (-)-Kaitocephalin http://www.organic-chemistry.org/Highlights/2013/28January. shtm January 28, 2013 19. C-H Functionalization http://www.organic-chemistry.org/Highlights/2013/16Septembe r.shtm September 16, 2013 20. Natural Product Synthesis by C-H Functionalization: (±)-Allokainic Acid (Wee), (-)-Cameroonan-7?-ol (Taber), (+)-Lithospermic Acid (Yu), (-)-Manabacanine (Kroutil), Streptorubin B and Metacycloprodigiosin (Challis) http://www.organic-chemistry.org/Highlights/2012/30January. shtm January 30, 2012 21. Natural Product Synthesis by C-H Functionalization: (-)-Zampanolide (Ghosh), Muraymycin D2 (Ichikawa), (+)-Sundiversifolide (Iwabuchi), (+)-Przewalskin B (Zhang/Tu), Artemisinin (Wu) http://www.organic-chemistry.org/Highlights/2012/11June.sht m June 11, 2012 Carbon-Carbon Bond Construction 22. Carbon-Carbon Bond Formation: The Bergman Synthesis of (+)-Fuligocandin B http://www.organic-chemistry.org/Highlights/2012/12March.sh tm March 12, 2012 23. C-C Bond Formation: The Petrov Synthesis of Combretastatin A-4 http://www.organic-chemistry.org/Highlights/2012/18June.sht m June 18, 2012 24. Carbon-Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol http://www.organic-chemistry.org/Highlights/2013/11March.sh tm March 11, 2013 25. Carbon-Carbon Bond Construction http://www.organic-chemistry.org/Highlights/2013/29July.sht m July 29, 2013 26. Reactions Involving C-C Bond Cleavage http://www.organic-chemistry.org/Highlights/2013/23Septembe r.shtm September 23, 2013 Reactions of Alkenes 27. Reactions of Alkenes: The RajanBabu Synthesis of Pseudopterosin G-J Aglycone Dimethyl Ether March 26, 2012 28. Reactions of Alkenes http://www.organic-chemistry.org/Highlights/2012/10Septembe r.shtm September 10, 2012 29. Reactions of Alkenes http://www.organic-chemistry.org/Highlights/2013/18March.sh tm March 18, 2013 30. Synthesis and Reactions of Alkenes http://www.organic-chemistry.org/Highlights/2013/09Septembe r.shtm September 9, 2013 31. Advances in Alkene Metathesis: The Kobayashi Synthesis of (+)-TMC-151C http://www.organic-chemistry.org/Highlights/2012/23January. shtm January 23, 2012 Enantioselective Construction of Acyclic Stereogenic Centers 32. Enantioselective Synthesis of Alcohols and Amines: The Ichikawa Synthesis of (+)-Geranyllinaloisocyanide http://www.organic-chemistry.org/Highlights/2012/13February .shtm February 13, 2012 33. Enantioselective Synthesis of Alcohols and Amines: The Fujii/Ohno Synthesis of (+)-Lysergic Acid http://www.organic-chemistry.org/Highlights/2012/16July.sht m July 16, 2012 34. Asymmetric C-Heteroatom Bond Formation http://www.organic-chemistry.org/Highlights/2013/11February .shtm February 11, 2013 35. Construction of Single Stereocenters http://www.organic-chemistry.org/Highlights/2013/15July.sht m July 15, 2013 36. Enantioselective Construction of Alkylated Centers: The Shishido Synthesis of (+)-Helianane http://www.organic-chemistry.org/Highlights/2012/20February .shtm February 20, 2012 37. Enantioselective Synthesis of Alkylated Centers: The Fukuyama Synthesis of (-)-Histrionicotoxin http://www.organic-chemistry.org/Highlights/2012/23July.sht m July 23, 2012 38. Asymmetric C-C Bond Formation http://www.organic-chemistry.org/Highlights/2013/18February .shtm February 18, 2013 39. Arrays of Stereogenic Centers: The Davies Synthesis of Acosamine http://www.organic-chemistry.org/Highlights/2012/27February .shtm February 27, 2012 40. Construction of Alkylated Stereocenters: The Deng Synthesis of (-)-Isoacanthodoral http://www.organic-chemistry.org/Highlights/2013/08July.sht m July 8, 2013 41. Arrays of Stereogenic Centers: The Barker Synthesis of (+)-Galbelgin http://www.organic-chemistry.org/Highlights/2012/30July.sht m July 30, 2012 42. Arrays of Stereogenic Centers: The Carbery Synthesis of Mycestericin G http://www.organic-chemistry.org/Highlights/2013/25February .shtm February 25, 2013 43. Construction of Stereochemical Arrays http://www.organic-chemistry.org/Highlights/2013/22July.sht m July 22, 2013 Construction of C-O Rings 44. Stereoselective C-O Ring Construction: The Keck Synthesis of Bryostatin 1 http://www.organic-chemistry.org/Highlights/2012/09January. shtm January 9, 2012 45. C-O Ring Construction: The Georg Synthesis of Oximidine II http://www.organic-chemistry.org/Highlights/2012/09April.sh tm April 9, 2012 46. C-O Ring Construction: The Reisman Synthesis of (-)-Acetylaranotin http://www.organic-chemistry.org/Highlights/2013/14January. shtm January 14, 2013 47. C-O Ring Formation http://www.organic-chemistry.org/Highlights/2013/08April.sh tm April 8, 2013 48. C-O Ring Construction: (+)-Varitriol (Liu), (+)-Isatisine A (Panek), (+)-Herboxidiene / GEX1A (Ghosh), (-)-Englerin A (Chain), Platensimycin (Lear/Wright) http://www.organic-chemistry.org/Highlights/2012/16January. shtm January 16, 2012 49. C-O Natural Products: (-)-Hybridalactone (Fürstner), (+)- Anthecotulide (Hodgson), (-)-Kumausallene (Tang), (±)-Communiol E (Kobayashi), (-)-Exiguolide (Scheidt), Cyanolide A (Rychnovsky) http://www.organic-chemistry.org/Highlights/2012/16April.sh tm April 16, 2012 50. C-O Ring Containing Natural Products http://www.organic-chemistry.org/Highlights/2013/21January. shtm January 21, 2013 51. Total Synthesis of C-O Ring-Containing Natural Products http://www.organic-chemistry.org/Highlights/2013/15April.sh tm April 15, 2013 Construction of C-N Rings 52. C-N Ring Construction: The Harrity Synthesis of Quinolizidine (-)-217A http://www.organic-chemistry.org/Highlights/2012/23April.sh tm April 23, 2012 53. New Methods for C-N Ring Construction http://www.organic-chemistry.org/Highlights/2012/19November .shtm November 19, 2012 54. C-N Ring Construction: The Fujii/Ohno Synthesis of (-)-Quinocarcin http://www.organic-chemistry.org/Highlights/2013/22April.sh tm April 22, 2013 55. C-N Ring Construction: The Hoye Synthesis of (±)-Leuconolactam http://www.organic-chemistry.org/Highlights/2013/18November .shtm November 18, 2013 56. Alkaloid Synthesis: (-)-?-Kainic Acid (Cohen), Hyacinthacine A2 (Fox), (-)-Agelastatin A (Hamada), (+)-Luciduline (Barbe), (+)-Lunarine (Fan), (-)-Runanine (Herzon) http://www.organic-chemistry.org/Highlights/2012/30April.sh tm April 30, 2012 57. Alkaloid Synthesis: Indolizidine 207A (Shenvi), (-)-Acetylaranotin (Reisman), Flinderole A (May), Isohaouamine B (Trauner), (-)-Strychnine (MacMillan) http://www.organic-chemistry.org/Highlights/2012/26November .shtm November 26, 2012 58. Alkaloid Synthesis: (+)-Deoxoprosopinine (Krishna), Alkaloid (-)-205B (Micalizio), FR901483 (Huang), (+)-Ibophyllidine (Kwon), (-)-Lycoposerramine-S (Fukuyama), (±)-Crinine (Lautens) http://www.organic-chemistry.org/Highlights/2013/29April.sh tm April 29, 2013 59. Alkaloid Synthesis: Lycoposerramine Z (Bonjoch), Esermethole (Shishido), Goniomitine (Zhu), Grandisine (Taylor), Reserpine (Jacobsen) http://www.organic-chemistry.org/Highlights/2013/25November .shtm November 25, 2013 Substituted Benzene Derivatives 60. Substituted Benzenes: The Reddy Synthesis of Isofregenedadiol http://www.organic-chemistry.org/Highlights/2012/25June.sht m June 25, 2012 61. Substituted Benzenes: The Alvarez-Manzaneda Synthesis of (-)-Akaol A http://www.organic-chemistry.org/Highlights/2012/08October. shtm October 8, 2012 62. Substituted Benzenes: The Subba Reddy Synthesis of 7-Desmethoxyfusarentin http://www.organic-chemistry.org/Highlights/2013/17June.sht m June 17, 2013 63. Substituted Benzenes: The Gu Synthesis of Rhazinal http://www.organic-chemistry.org/Highlights/2013/14October. shtm October 14, 2013 Heteroaromatic Derivatives 64. Heteroaromatic Construction: The Sperry Synthesis of (+)-Terreusinone http://www.organic-chemistry.org/Highlights/2012/09July.sht m July 9, 2012 65. Heteroaromatic Construction: The Sato Synthesis of (-)-Herbindole http://www.organic-chemistry.org/Highlights/2012/15October. shtm October 15, 2012 66. Advances in Heterocyclic Aromatic Construction http://www.organic-chemistry.org/Highlights/2013/24June.sht m June 24, 2013 67. Synthesis of Heteroaromatics http://www.organic-chemistry.org/Highlights/2013/21October. shtm October 21, 2013 Organocatalyzed C-C Ring Construction 68. Organocatalytic Carbocyclic Construction: The You Synthesis of (-)-Mesembrine http://www.organic-chemistry.org/Highlights/2012/20August.s htm August 20, 2012 69. Organocatalyzed Carbocyclic Construction: (+)-Roseophilin (Flynn) and (+)-Galbulin (Hong) http://www.organic-chemistry.org/Highlights/2012/10December .shtm December 10, 2012 70. Organocatalytic C-C Ring Construction: Prostaglandin F2? (Aggarwal) http://www.organic-chemistry.org/Highlights/2013/12August.s htm August 12, 2013 71. Organocatalyzed C-C Ring Construction: The Hayashi Synthesis of PGE1 Me Ester http://www.organic-chemistry.org/Highlights/2013/16December .shtm December 16, 2013 Metal-Mediated C-C Ring Construction 72. Metal-Mediated Carbocyclic Construction: The Chen Synthesis of Ageliferin http://www.organic-chemistry.org/Highlights/2012/13August.s htm August 13, 2012 73. Metal-Mediated Carbocyclic Construction: The Whitby Synthesis of (+)-Mucosin http://www.organic-chemistry.org/Highlights/2012/17December .shtm December 17, 2012 74. Metal-Mediated C-C Ring Construction: (+)-Shiromool (Baran) http://www.organic-chemistry.org/Highlights/2013/19August.s htm August 19, 2013 75. Metal-Mediated Ring Construction: The Hoveyda Synthesis of (-)-Nakadomarin A http://www.organic-chemistry.org/Highlights/2013/09December .shtm December 9, 2013 Intermolecular and Intramolecular Diels-Alder Reactions 76. Intramolecular Diels-Alder Cycloaddition: 7-Isocyanoamphilecta-11(20),15-diene (Miyaoka), (-)-Scabronine G (Kanoh), Basiliolide B (Stoltz), Hirsutellone B (Uchiro), Echinopine A (Chen) http://www.organic-chemistry.org/Highlights/2012/27August.s htm August 27, 2012 77. Diels-Alder Cycloaddition: Fawcettimine (Williams), Apiosporic Acid (Helmchen), Marginatone (Abad-Somovilla), Okilactomycin (Hoye), Vinigrol (Barriault), Plakotenin (Bihlmeier/Klopper) http://www.organic-chemistry.org/Highlights/2012/24December .shtm December 24, 2012 78. Diels-Alder Cycloaddition: Defucogilvocarcin V (Bodwell), (+)-Carrisone (Danishefsky), (+)-Fusarisetin A (Theodorakis), 9?-Presilphiperfolan-1?-ol (Stoltz), 7-Isocyano-11(20), 14-epiamphilectadiene (Shenvi) http://www.organic-chemistry.org/Highlights/2013/26August.s htm August 26, 2013 79. Diels-Alder Cycloaddition: (+)-Armillarivin (Banwell), Gelsemiol (Gademann), (+)-Frullanolide (Liao), Myceliothermophin A (Uchiro), Peribysin E (Reddy), Caribenol A (Li/Yang) http://www.organic-chemistry.org/Highlights/2013/23December .shtm December 23, 2013 Stereocontrolled C-C Ring Construction 80. Chloranthalactone (Liu), Rumphellaone A (Kuwahara), Lactiflorin (Bach), Echinosporin (Hale), Harveynone (Taylor), (6,7-deoxy)-Yuanhuapin (Wender) http://www.organic-chemistry.org/Highlights/2012/31December .shtm December 31, 2012 81. Other Methods for C-C Ring Construction: The Liang Synthesis of Echinopine B http://www.organic-chemistry.org/Highlights/2013/30December .shtm December 30, 2013 Classics in Total Synthesis 82. The Reisman Synthesis of (+)-Salvileucalin B http://www.organic-chemistry.org/Highlights/2012/02January. shtm January 2, 2012 83. The Theodorakis Synthesis of (-)-Jiadifenolide http://www.organic-chemistry.org/Highlights/2012/06February .shtm February 6, 2012 84. The Yamashita/Hirama Synthesis of Cortistatin A http://www.organic-chemistry.org/Highlights/2012/05March.sh tm March 5, 2012 85. The Reisman Synthesis of (-)-Maoecrystal Z http://www.organic-chemistry.org/Highlights/2012/02April.sh tm April 2, 2012 86. The Tan/Chen/Yang Synthesis of Schindilactone A http://www.organic-chemistry.org/Highlights/2012/07May.shtm May 7, 2012 87. The Garg Synthesis of (-)-N-Methylwelwitindolinone C http://www.organic-chemistry.org/Highlights/2012/04June.sht m June 4, 2012 88. The Krische Synthesis of Bryostatin 7 http://www.organic-chemistry.org/Highlights/2012/02July.sht m July 2, 2012 89. The Fukuyama Synthesis of Gelsemoxonine http://www.organic-chemistry.org/Highlights/2012/06August.s htm August 6, 2012 90. The Carreira Synthesis of (+)-Daphmanidin E http://www.organic-chemistry.org/Highlights/2012/03Septembe r.shtm September 3, 2012 91. The Qin Synthesis of (+)-Gelsemine http://www.organic-chemistry.org/Highlights/2012/01October. shtm October 1, 2012 92. The Carreira Synthesis of Indoxamycin B http://www.organic-chemistry.org/Highlights/2012/05November .shtm November 5, 2012 93. The Nicolaou/Li Synthesis of Tubingensin A http://www.organic-chemistry.org/Highlights/2012/03December .shtm December 3, 2012 94. The Thomson Synthesis of (-)-GB17 http://www.organic-chemistry.org/Highlights/2013/07January. shtm January 7, 2013 95. The Li Synthesis of (-)-Fusarisetin A http://www.organic-chemistry.org/Highlights/2013/04February .shtm February 4, 2013 96. The Carreira Synthesis of (-)-Dendrobine http://www.organic-chemistry.org/Highlights/2013/04March.sh tm March 4, 2013 97. The Vanderwal Synthesis of Echinopine B http://www.organic-chemistry.org/Highlights/2013/01April.sh tm April 1, 2013 98. The Dixon Synthesis of Manzamine A http://www.organic-chemistry.org/Highlights/2013/06May.shtm May 6, 2013 99. The Williams Synthesis of (-)-Khayasin http://www.organic-chemistry.org/Highlights/2013/03June.sht m June 3, 2013 100. The Kuwahara Synthesis of Paspalinine http://www.organic-chemistry.org/Highlights/2013/01July.sht m July 1, 2013 101. The Ma Synthesis of Gracilamine http://www.organic-chemistry.org/Highlights/2013/05August.s htm August 5, 2013 102. The Carreira Synthesis of (±)-Gelsemoxonine http://www.organic-chemistry.org/Highlights/2013/02Septembe r.shtm September 2, 2013 103. The Evans Synthesis of (-)-Nakadomarin A http://www.organic-chemistry.org/Highlights/2013/07October. shtm October 7, 2013 104. The Procter Synthesis of (+)-Pleuromutilin http://www.organic-chemistry.org/Highlights/2013/04November .shtm November 4, 2013 105. The Harran Synthesis of (+)-Roseophilin http://www.organic-chemistry.org/Highlights/2013/02December .shtm December 2, 2013