Table of Contents

Preface

Organic Functional Group Interconversion and Protection

1. Organic Functional Group Interconversion

2. Organic Functional Group Interconversion

3. Organic Functional Group Interconversion

4. Oxidation

5. Functional Group Oxidation and Reduction

6. Oxidation of Organic Functional Groups

7. New Methods for Reduction and for Oxidation

8. Reductions

9. Reduction of Organic Functional Groups

10. Organic Functional Group Protection

11. Organic Functional Group Protection and Deprotection

12. Organic Functional Group Protection

13. Functional Group Protection: The Pohl Synthesis of b-1,4-Mannuronate Oligomers

Flow Methods

14. Flow Chemistry: The Direct Production of Drug Metabolites

15. Developments in Flow Chemistry

16. Flow Chemistry

C-H Functionalization

17. Selective Functionalization of C-H Bonds

18. C-H Functionalization: The Snyder Synthesis of (+)-Scholarisine A

19. C-H Functionalization: The Maimone Synthesis of Podophyllotoxin

20. C-H Functionalization: The Shaw Synthesis of E-d-Viniferin

Carbon-Carbon Bond Construction

21. C-C Bond Construction: The Zhu Synthesis of Goniomitine

22. C-C Bond Construction: The Kingsbury Synthesis of (-)-Dihydrocuscohygrine

23. C-C Bond Construction: The Galano Synthesis of 8-F3t-Isoprostane

24. C-C Bond Construction: The Hou Synthesis of (-)-Brevipolide H

Reactions of Alkenes

25. Alkenes

26. Alkene Reactions: The Xu/Loh Synthesis of Vitamin A1

27. Reactions of Alkenes

28. Reactions of Alkenes: The Usami Synthesis of (-)-Pericosine E

Enantioselective Construction of Acyclic Stereogenic Centers

29. Construction of Single Stereocenters

30. Enantioselective Synthesis of Alcohols and Amines: The Zhu Synthesis of (+)-Trigonoliimine A

31. Enantioselective Synthesis of Alcohols and Amines: The Kim Synthesis of (+)-Frontalin

32. Enantioselective Synthesis of Alcohols and Amines: The Doi Synthesis of Apratoxin C

33. Construction of Alkylated Stereocenters

34. Enantioselective Construction of Alkylated Centers: The Rawal Synthesis of (+)-Fornicin C

35. Alkylated Stereogenic Centers: The Jia Synthesis of (-)-Goniomitine

36. Construction of Alkylated Stereogenic Centers: The Zhu Synthesis of (-)-Rhazinilam

37. Construction of Multiple Stereocenters

38. Arrays of Stereogenic Centers: The Yadav Synthesis of Nhatrangin A

39. Arrays of Stereogenic Centers: The Thomson Synthesis of (-)-Galcatin

40. Arrays of Stereogenic Centers: The Shin/Chandrasekhar Synthesis of (+)-Lactacystin

Construction of C-O Rings

41. C-O Ring Construction. The Martín and Martín Synthesis of Teurilene

42. C-O Ring Formation

43. C-O Ring Construction: The Tong Synthesis of (-)-Aculeatin A

44. C-O Ring Construction: The Smith Synthesis of (+)-18-epi-Latrunculol A

45. C-O Ring Construction: The Oger/Lee/Galano Synthesis of 7(RS)-ST-D8-11-dihomo-Isofuran

46. C-O Ring-Containing Natural Products: Cyanolide A (Krische), Bisabosqual A (Parker), Iso-Eriobrucinol A (Hsung), Trichodermolide A (Hiroya), Batrachotoxin Core (Du Bois)

47. Total Synthesis of C-O Natural Products

48. C-O Natural Products: DihomoIsoF (Lee/Galano), Pyrenolide D (Gracza), Clavilactone A (Li), Psoracorylifol A (Tong), Bermudenynol (Kim), Aspercyclide C (Hirama)

49. C-O Ring Construction: Sauropus hexoside (Xie/Wu), (+)-Ipomeamarone (Usuki), Decytospolide A (Fujioka), Cytospolide P (Goswami), (+)-Didemniserinolipid B (Tong), Gymnothelignan N (She)

50. C-O Ring Containing Natural Products: (+)-Isatisine A (Panek), Cephalasporolide E (Sartillo-Piscil), (+)-Xestodecalactone (Jennings), Colchilomycin B (Banwell), Lactimidomycin (Georg), 5,6-Dihydrocineromycin B (Fürstner)

Construction of C-N Rings

51. C-N Ring Construction: The Waser Synthesis of Jerantinine E

52. C-N Ring Construction: The Glorius Synthesis of ent-Monomorine

53. C-N Ring Construction: The Weinreb Synthesis of Myrioneurinol

54. C-N Ring Construction: The Hattori Synthesis of (+)-Spectaline

55. Alkaloid Synthesis: (-)-L-Batzellaside A (Toyooka), Limazepine A (Zemribo), (+)-Febrifugine (Pansare), Amathaspiramide F (Tambar), Allomatrine (Brown), Lyconadine C (Waters), Tabersonine (Andrade)

56. Alkaloid Synthesis: Penaresidin A (Subba Reddy), Allokainic Acid (Saicic), Sedacryptine (Rutjes), Lepistine (Yokoshima/Fukuyama), Septicine (Hanessian), Lyconadin C (Dai)

57. Alkaloid Synthesis: Indolizidine 223AB (Cha), Lepadiformine (Kim), Kainic Acid (Fukuyama), Gephyrotoxin (Smith), Premarineosin A (Reynolds)

58. Alkaloid Synthesis: (-)-a-Kainic Acid (Ohshima), Serpentine (Scheidt), (-)-Galanthamine (Jia), (+)-Trigolutes B (Gong), Sarain A (Yokoshima/Fukuyama), DZ-2384 (Harran)

Substituted Benzene Derivatives

59. Preparation of Benzene Derivatives: The Yu/Baran Synthesis of (+)-Hongoquercin A

60. Substituted Benzenes: The Garg Synthesis of Tubingensin A

61. Substituted Benzenes: The Li Synthesis of Rubriflordilactone A

62. Preparation of Substituted Benzenes: The Beaudry Synthesis of Arundamine

Heteroaromatic Derivatives

63. Preparation of Heterocycles: The Boukouvalas Synthesis of (-)-Auxofuran

64. Heteroaromatic Synthesis: The Tokuyama Synthesis of (-)-Rhazinilam

65. Heteroaromatics: The Zhou/Li Synthesis of Goniomitine

66. Heteroaromatic Construction: The Li Synthesis of Mycoleptodiscin A

Organocatalyzed C-C Ring Construction

67. Organocatalyzed C-C Ring Construction: The Carreira Synthesis of (+)-Crotogoudin

68. Organocatalyzed C-C Ring Construction: The Jørgenson Synthesis of (+)-Estrone

69. Organocatalyzed C-C Ring Construction: The Bradshaw/Bonjoch Synthesis of (-)-Cermizine B

70. Organocatalyzed C-C Ring Construction: The Mihovilovic Synthesis of Piperenol B

Metal-Mediated C-C Ring Construction

71. Metal-mediated C-C Ring Construction: The Carreira Synthesis of (+)-Asperolide C

72. Metal-Mediated C-C Ring Construction: The Sun/Lin Synthesis of Huperzine A

73. Metal-Mediated C-C Ring Construction: The Ding Synthesis of (-)-Indoxamycin B

74. Metal-Mediated C-C Ring Construction: The Lei Synthesis of (-)-Huperzine Q

Intermolecular and Intramolecular Diels-Alder Reactions

75. Diels-Alder Cycloaddition: Pancratistatin (Cho), Reddy (Nootkatone), Zhang/Lee (Platensimycin), Nakada (Scabronine G), Isoglaziovianol (Trauner)

76. Diels-Alder Cycloaddition: Fawcettimine (Zhai), Sculponeatin N (Zhai), Elansolid B1 (Kirschning), Frondosin A (Wright), Kingianin H (Parker), Rufescenolide (Snyder)

77. Diels-Alder Cycloaddition: Nicolaioidesin B (Coster), Lycorine (Cho), Bucidarasin A (Nakada), Maoecrystal V (Thomson), Kuwanon J (Wulff/Lei), Vinigrol (Kaliappan)

78. Diels-Alder Cycloaddition: Sarcandralactone A (Snyder), Pseudopterosin (-)-G-J aglycone (Paddon-Row/Sherburn), IBIR-22 (Westwood), Muironolide A (Zakarian), Platencin (Banwell), Chatancin (Maimone)

Stereocontrolled C-C Ring Construction

79. Other Methods for C-C Ring Construction: Pinolinone (Bach), Agelastatin A (Batey), Panaginsene (Lee), Salvileucalin D, Salvileucalin C (Ding), ent-Codeine (Hudlicky), Walsucochin B (Xie/Shi)

80. Carbocyclic Ring Construction: The Nicolaou Synthesis of Myceliothermophin E

Classics in Total Synthesis

81. The Inoue Synthesis of 19-Hydroxysarmentogenin

82. The Nakada Synthesis of (+)-Ophiobolin A

83. The Herzon Synthesis of (-)-Acutumine

84. The Njardarson Synthesis of Vinigrol

85. The Gin Synthesis of Neofinaconitine

86. The Li Synthesis of Daphenylline

87. The Baran Synthesis of Ingenol

88. The Fürstner Synthesis of Amphidinolide F

89. The Deslongchamps Synthesis of (+)-Cassaine

90. The Kan Synthesis of the Streptomyces Alkaloid SB-203207

91. The Trost Synthesis of (-)-Lasonolide A

92. The Fukuyama Synthesis of (-)-Lepenine

93. The Smith Synthesis of (-)-Calyciphylline N

94. The Paterson Synthesis of (-)-Leiodermatolide

95. The Fuwa Synthesis of Didemnaketal B

96. The Lee Synthesis of (-)-Crinipellin A

97. The Snyder Synthesis of Psylloborine A

98. The Morken Synthesis of (+)-Discodermolide



99. The Trauner Synthesis of (-)-Nitidasin

100. The Hoveyda Synthesis of Disorazole C1

101. The Smith Synthesis of (-)-Nodulisporic Acid D

102. The Sato/Chida Synthesis of Paclitaxel (Taxol®)

103. The Johnson Synthesis of Paspaline

104. The Ding Synthesis of Steenkrotin A

About the Author

Doug Taber is a Professor of Chemistry and Biochemistry at University of Delaware. He is an OUP author of three books in the Organic Synthesis series.

Tristan Lambert is an Associate Professor of Chemistry at Columbia University.