Discovery of Novel Synthetic Methodologies and Reagents during Natural Product Synthesis in the Post-Palytoxin Era

Chemical Reviews

Volumn 115, Issue 17, 2015, Pages 9232-9276

  Armaly, Ahlam M ^a   Deporre, Yvonne C ^a   Groso, Emilia J ^a   Riehl, Paul S ^a   Schindler, Corinna S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENTS; SYNTHESIS (CHEMICAL);

C-C BOND FORMING REACTION; HARVARD UNIVERSITY; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; SODIUM-POTASSIUM PUMP; SYNTHETIC METHODOLOGY; SYNTHETIC METHODS; TOTAL SYNTHESIS;

POLYOLS;

ACRYLAMIDE DERIVATIVE; BIOLOGICAL PRODUCT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PALYTOXIN;

CHEMISTRY; HISTORY; SYNTHESIS;

ACRYLAMIDES; BIOLOGICAL PRODUCTS; CHEMISTRY TECHNIQUES, SYNTHETIC; HISTORY, 20TH CENTURY; HISTORY, 21ST CENTURY; INDICATORS AND REAGENTS;

EID: 84941130834     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/acs.chemrev.5b00034     Document Type: Review

References (271)

1. Eschenmoser, A.; Wintner, C. E. Natural Product Synthesis and Vitamin B12 Science 1977, 196, 1410-1420
2. Pelletier, P. J.; Caventou, J. B. Note sur un nouvel Alcali Ann. Chim. Phys. 1818, 8, 323
3. Pelletier, P. J.; Caventou, J. B. Sur un nouvel Alcali végétal (la Strychnine) trouve dans la fève de Saint-Ignace, la noix vomique, etc Ann. Chim. Phys. 1819, 10, 142
4. Prelog, V.; Szpilfogel, S. Strychnos-Alkaloide. (2. Mitteilung). Abbauversuche im ringe E des Strychnins Helv. Chim. Acta 1945, 28, 1669-1677
5. Prelog, V.; Kocór, M. Strychnos-Alkaloide. (4. Mitteilung). Über die Lage der Oxy-Gruppe in Pseudostrychnin Helv. Chim. Acta 1947, 30, 359-366
6. 2. Helv. Chim. Acta 1948, 31, 237-241
7. Briggs, L. H.; Openshaw, T. H.; Robinson, R. Strychnine and brucine. Part XLII. Constitution of the neo-series of bases and their oxidation products J. Chem. Soc. 1946, 903-908
8. Robinson, R. The Constitution of Strychnine Experientia 1946, 2, 28-29
9. Anet, F. A. L.; Robinson, R. Conversion of the Wieland-Gumlich aldehyde into strychnine Chem. Ind. 1953, 245
10. Anet, F. A. L.; Robinson, R. Alkaloids of Australian Strychnos species. Part II. The constitution of strychnospermine and spermostrychnine J. Chem. Soc. 1955, 2253-2262
11. Leuchs, H. Über Strychnon und Pseudo-strychnon als Nebenproduckte der Darstellung des Pseudo-strychnins und über weitere Versuche in dessen Reihe. (Teilweise mit Fritz Räck.) (über Strychnos-Alkaloide, 110. Mitteil.) Chem. Ber. 1940, 73, 731-739
12. Woodward, R. B.; Brehm, W. J.; Nelson, A. L. The Structure of Strychnine J. Am. Chem. Soc. 1947, 69, 2250
13. Woodward, R. B.; Brehm, W. J. The Structure of Strychnine. Formulation of the Neo Bases J. Am. Chem. Soc. 1948, 70, 2107-2115
14. Robertson, J. H.; Beevers, C. A. The Crystal Structure of Strychnine Hydrogen Bromide Acta Crystallogr. 1951, 4, 270-275
15. Bokhoven, C.; Schoone, J. C.; Bijvoet, J. M. The Fourier Synthesis of the Crystal Structure of Strychnine Sulfate Pentahydrate Acta Crystallogr. 1951, 4, 275-280
16. Peerdeman, A. F. The Absolute Configuration of Natural Strychnine Acta Crystallogr. 1956, 9, 824
17. Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Dafniker, H. U.; Schenker, K. The Total Synthesis of Strychnine Tetrahedron 1963, 19, 247-288
18. Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. The Total Synthesis of Strychnine J. Am. Chem. Soc. 1954, 76, 4749-4751
19. Woodward, R. B. Harvey Lect. 1963, 59, 31-47
20. Pelletier, P. J.; Caventou, J. B. Examen chimique de plusieurs végétaux de la famille des colchicées, et du principe actif quils renferment Ann. Chim. Phys. 1820, 14, 69-81
21. Dewar, M. J. S. Structure of Colchicine Nature 1945, 141-142
22. Schreiber, J.; Leimgruber, W.; Pesaro, M.; Schudel, P.; Eschenmoser, A. Synthese des Colchicins Angew. Chem. 1959, 71, 637-640
23. Van Tamelen, E. E.; Spencer, T. A., Jr.; Allen, D. S., Jr.; Orvis, R. L. The Total Synthesis of Colchicine J. Am. Chem. Soc. 1959, 81, 6341
24. Sunagawa, G.; Nakamura, T.; Nakazawa, J. Studies on the Total Synthesis of dl-Colchiceine. II. Synthesis of dl-Demethoxydeoxyhexahydrocolchiceine Chem. Pharm. Bull. 1962, 10, 291-299
25. Overman, L. E. Molecular Rearrangements in the Construction of Complex Molecules Tetrahedron 2009, 65, 6432-6446
26. Service, R. F. Race for Molecular Summits Science 1999, 285, 184-187
27. Woodward, R. B. Recent advances in the chemistry of natural products Pure Appl. Chem. 1968, 17, 519-547
28. Woodward, R. B. Recent advances in the chemistry of natural products Pure Appl. Chem. 1971, 25, 283-304
29. Woodward, R. B. The total synthesis of vitamin B12 Pure Appl. Chem. 1973, 33, 145-178
30. Eschenmoser, A. Studies on the synthesis of corrins Pure Appl. Chem. 1963, 7, 297-316
31. Eschenmoser, A. Organische Naturstoffsynthese heute. Vitamin B12 als Beispiel Naturwissenschaften 1974, 61, 513-525
32. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry Angew. Chem., Int. Ed. Engl. 1969, 8, 781-853
33. Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWhorter, W. W., Jr.; Mizuno, M.; Nakata, M.; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, K.; Uenishi, J.; White, J. B.; Yonaga, M. Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide J. Am. Chem. Soc. 1989, 111, 7530-7533
34. Suh, E. M.; Kishi, Y. Synthesis of Palytoxin from Palytoxin Carboxylic Acid J. Am. Chem. Soc. 1994, 116, 11205-11206
35. Moore, R. E.; Scheuer, P. J. Palytoxin: A New Marine Toxin from a Coelenterate Science 1971, 172, 495-498
36. Uemura, D.; Ueda, K.; Hirata, Y.; Naoki, H.; Iwashita, T. Further Studies on Palytoxin. II. Structure of Palytoxin Tetrahedron Lett. 1981, 22, 2781-2784
37. Moore, R. E.; Bartolini, G. Structure of Palytoxin J. Am. Chem. Soc. 1981, 103, 2491-2494
38. Cha, J. K.; Christ, W. J.; Finan, J. M.; Fujioka, H.; Kishi, Y.; Klein, L. L.; Ko, S. S.; Leder, J.; McWhorter, W. W., Jr.; Pfaff, K.-P.; Yonaga, M.; Uemura, D.; Hirata, Y. Stereochemistry of Palytoxin. Part 4. Complete Structure J. Am. Chem. Soc. 1982, 104, 7369-7371
39. Wu, C. H. Palytoxin: Membrane Mechanisms of Action Toxicon 2009, 54, 1183-1189
40. Crawford, M. H. Harvard Synthesizes Palytoxin Molecule Science 1989, 246, 34
41. Kishi, Y. Natural Products Synthesis: Palytoxin Pure Appl. Chem. 1989, 61, 313-324
42. Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. Catalytic Effect of Nickel(II) Chloride and Palladium(II) Acetate on Chromium(II)-Mediated Coupling Reaction of Iodo Olefins with Aldehydes J. Am. Chem. Soc. 1986, 108, 5644-5646
43. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Selective Grignard-type Carbonyl Addition of Alkenyl Halides Mediated by Chromium(II) Chloride Tetrahedron Lett. 1983, 24, 5281-5284
44. Fuerstner, A.; Shi, N. Nozaki-Hiyama-Kishi Reactions Catalytic in Chromium J. Am. Chem. Soc. 1996, 118, 12349-12357
45. Trost, B. M. The Atom Economy: A Search for Synthetic Efficiency Science 1991, 254, 1471-1477
46. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Function-Oriented Synthesis, Step Economy, and Drug Design Acc. Chem. Res. 2008, 41, 40-49
47. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Redox Economy in Organic Synthesis Angew. Chem., Int. Ed. 2009, 48, 2854
48. Wender, P. A.; Miller, B. L. Synthesis at the Molecular Frontier Nature 2009, 460, 197-201
49. Denmark, S. E. The Interplay of Invention, Discovery, Development, and Application in Organic Synthetic Methodology: A Case Study J. Org. Chem. 2009, 74, 2915-2867
50. Zhang, Y.; Rainier, J. D. Two-Directional Olefinic-Ester Ring-Closing Metathesis using Reduced Ti Alkylidenes: A Rapid Entry into Polycyclic Ether Skeletons Org. Lett. 2009, 11, 237
51. Ng, S. M.; Beaudry, C. M.; Trauner, D. Intramolecular Diels-Alder Reactions of 5-Vinyl-1,3-cyclohexadienes Org. Lett. 2003, 5, 1701
52. Dabrah, T. T.; Kaneko, T.; Massefski, W., Jr.; Whipple, E. B. CP-225,917 and CP-263,114: Novel Ras Farnesylation Inhibitors from an Unidentified Fungus. 2. Structure Elucidation J. Am. Chem. Soc. 1997, 119, 1594-1598
53. Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Synthesis of the Bicyclic Core of CP-225,917 and CP-263,114 by an Intramolecular Diels Alder Reaction Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196
54. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Yoon, W. H.; He, Y.; Fong, K. C. Total Synthesis of the CP- Molecules CP-263,114 and CP-225,917, Part 1: Synthesis of Key Intermediates and Intelligence Gathering Angew. Chem., Int. Ed. 1999, 38, 1669-1675
55. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H.-S. Total Synthesis of the CP- Molecules CP-263,114 and CP-225,917, Part 2: Evolution of the Final Strategy Angew. Chem., Int. Ed. 1999, 38, 1676-1678
56. Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. A Novel Approach to the CP-225,917 and CP-263,114 Core Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823
57. Nicolaou, K. C.; He, Y.; Fong, K. C.; Yoon, W. H.; Choi, H.-S.; Zhong, Y.-L.; Baran, P. S. Novel Strategies to Construct the γ-Hydroxy Lactone Moiety of the CP Molecules. Synthesis of the CP-225,917 Core Skeleton Org. Lett. 1999, 1, 63-66
58. Nicolaou, K. C.; Baran, P. S.; Jautelat, R.; He, Y.; Fong, K. C.; Choi, H.-S.; Yoon, W. H.; Zhong, Y.-L. A Novel Route to the Fused Maleic Anhydride Moiety of CP Molecules Angew. Chem., Int. Ed. 1999, 38, 549-552
59. Nicolaou, K. C.; Jung, J.-K.; Yoon, W. H.; He, Y.; Zhong, Y.-L.; Baran, P. S. The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A) Angew. Chem., Int. Ed. 2000, 39, 1829-1832
60. Waizumi, N.; Itoh, T.; Fukuyama, T. Synthetic Studies on CP-225,917 and CP-263,114 Tetrahedron Lett. 1998, 39, 6015-6018
61. Waizumi, N.; Itoh, T.; Fukuyama, T. Total Synthesis of (-)-CP-263,114 (Phomoidride B) J. Am. Chem. Soc. 2000, 122, 7825-7826
62. Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; DAmico, D. C.; Danishefsky, S. J. Total Syntheses of CP-225,917 and CP-263,114: Creation of a Matrix Structure by Sequential Aldol Condensation and Intramolecular Heck Ring Closure Angew. Chem., Int. Ed. 1998, 37, 1877-1880
63. Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; DAmico, D. C.; Danishefsky, S. J. A Stereospecific Geminal Alkylation Scheme en Route to CP-225,917 and CP-263,114 Angew. Chem., Int. Ed. 1998, 37, 1880-1882
64. Meng, D.; Danishefsky, S. J. Stereospecific Sulfur-Mediated Cleavage of a Spirocyclobutanone: Synthesis of a Fully Functional Precursor to the CP Compounds Angew. Chem., Int. Ed. 1999, 38, 1485-1488
65. Tan, Q.; Danishefsky, S. J. The Synthesis of CP-263,114 and CP-225,917: Striking Long-Range Stereocontrol in the Fashioning of C7 Angew. Chem., Int. Ed. 2000, 39, 4509-4511
66. Ohmori, N. Synthetic Study of Phomoidride B (CP-263,114); Utilization of the Oxidopyrylium [5 + 2] Cycloaddition Chem. Commun. 2001, 1552-1553
67. Ohmori, N. Application of [5 + 2] Cycloaddition toward the Functionalized Bicyclo[4.3.1]decane Ring System: Synthetic Study of Phomoidride B (CP-263,114) J. Chem. Soc., Perkin Trans. 1 2002, 755-767
68. Isakovic, L.; Ashenhurst, J. A.; Gleason, J. L. Application of Lewis Acid Catalyzed Tropone [6 + 4] Cycloadditions to the Synthesis of the Core of CP-225,917 Org. Lett. 2001, 3, 4189-4192
69. Sgarbi, P. W. M.; Clive, D. L. J. Synthesis of the Carbobicyclic Substructure of CP-225,917 and CP-263,114 Chem. Commun. 1997, 2157-2158
70. Clive, D. L. J.; Zhang, J. Model Studies Related to CP-225,917: Stereocontrolled Generation of the Quaternary Center Tetrahedron 1999, 55, 12059-12068
71. Clive, D. L. J.; Sun, S.; He, X.; Zhang, J.; Gagliardini, V. Synthesis of the Tricyclic Bridgehead Olefins Related to the Core Structure of CP-225,917 and CP-263,114: Solvent, Strain, and Substitution Effects on Siloxy-Cope Rearrangments Tetrahedron Lett. 1999, 40, 4605-4609
72. Clive, D. L. J.; Sun, S. Synthesis of the Racemic Tetracyclic Core of CP-225,917, a Model Compound Lacking the Sidearms of the Natural Product Tetrahedron Lett. 2001, 42, 6267-6270
73. Clive, D. L. J.; Ou, L. Synthesis of the Racemic Tetracyclic Core of CP-225,917: Use of a Strain-Assisted Cope Rearrangment Tetrahedron Lett. 2002, 43, 4559-4563
74. Malihi, F.; Clive, D. L. J.; Chang, C.-C. Synthetic Studies on CP-225,917 and CP-263,114: Access to Advanced Tetracyclic Systems by Intramolecular Conjugate Displacement and [2,3]-Wittig Rearrangement J. Org. Chem. 2013, 78, 996-1013
75. Bio, M. M.; Leighton, J. L. An Approach to the Synthesis of the Phomoidrides J. Org. Chem. 2003, 68, 1693-1700
76. Banwell, M. G.; McRae, K. J.; Willis, A. C. A Chemoenzymatic Synthesis of the Carbobicyclic Core Associated with CP-225,917 and CP-263,114 (Phomoidrides A and B) J. Chem. Soc., Perkin Trans. 1 2001, 2194-2203
77. Banwell, M. G.; Coster, M. J.; Edwards, A. J.; Vögtle, M. CP-225,917 and CP-263,114 Synthesis Support Studies: Testing a Radical Cyclization Strategy for Installation of the Side-Chains Aust. J. Chem. 2003, 56, 577-583
78. Davies, H. M. L.; Calvo, R.; Ahmed, G. Type II Intramolecular Annulations between Vinylcarbenoids and Furans Tetrahedron Lett. 1997, 38, 1737-1740
79. Davies, H. M. L.; Ren, P. Dihydro- and Tetrahydrofuran Ring-Opening Reactions Directed towards the Synthesis of CP-263,114 Tetrahedron Lett. 2000, 41, 9021-9024
80. Davies, H. M. L.; Calvo, R. L.; Townsend, R. J.; Ren, P.; Churchill, R. M. An Exploratory Study of Type II [3 + 4] Cycloadditions between Vinylcarbenoids and Dienes J. Org. Chem. 2000, 65, 4261-4268
81. Armstrong, A.; Critchley, T. J.; Mortlock, A. A. Synthesis of the Bicyclo[4.4.1]decenone Core of CP-225,917 and CP-263,114 Synlett 1998, 552-553
82. Armstrong, A.; Critchley, T. J.; Gourdel-Marting, M.-E.; Kelsey, R. D.; Mortlock, A. A. Synthetic Studies on CP-225,917 and CP-263,114: Concise Synthesis of the Bicyclic Core Using an Intramolecular Mukaiyama Aldol Reaction J. Chem. Soc., Perkin Trans 1 2002, 1344-1350
83. Armstrong, A.; Critchley, T. J.; Gourdel-Martin, M.-E.; Kelsey, R. D.; Mortlock, A. A. Approaches to the γ-Lactone Unit of CP-225,917 and CP-263,114 Tetrahedron Lett. 2002, 43, 6027-6030
84. Armstrong, A.; Davies, N. G. M.; Martin, N. G.; Rutherford, A. P. Evaluation of Asymmetric Diels-Alder Approaches for the Synthesis of the Cyclohexene Subunit of CP-225,917 and CP263,114 Tetrahedron Lett. 2003, 44, 3915-3918
85. Yoshimitsu, T.; Yanagiya, M.; Nagaoka, H. An Approach to the Synthesis of CP-263,114: Complementary Routes to the Bicyclic Ring System via Two Kinds of Fragmentation Reaction Tetrahedron Lett. 1999, 40, 5215-5218
86. Yoshimitsu, T.; Yanagisawa, S.; Nagaoka, H. Asymmetric Synthesis of the Core Structure of (-)-CP-263,114 Org. Lett. 2000, 2, 3751-3754
87. Yoshimitsu, T.; Sasaki, S.; Arano, Y.; Nagaoka, H. Studies on the Total Synthesis of (-)-CP-263,114 J. Org. Chem. 2004, 69, 9262-9268
88. Crimmins, M. T.; Hauser, E. B. Synthesis of Crossed [2 + 2] Photocycloadducts: A Novel Approach to the Synthesis of Bridged Bicyclic Alkenes Org. Lett. 2000, 2, 281-284
89. Spiegel, D. A.; Njardarson, J. T.; Wood, J. L. CP-263,114 Synthetic Studies. Construction of an Isotwistane Ring System via Rhodium Carbenoid C-H Insertion Tetrahedron 2002, 58, 6545-6554
90. Murphy, G. K.; Shirahata, T.; Hama, N.; Bedermann, A.; Dong, P.; McMahon, T. C.; Twenter, B. M.; Spiegel, D. A.; McDonald, I. M.; Taniguchi, N.; Inoue, M.; Wood, J. L. Toward the Synthesis of Phomoidride D J. Org. Chem. 2013, 78, 477-489
91. Matsushita, T.; Ashida, H.; Kimachi, T.; Takemoto, Y. Synthetic Study on CP-263,114 (Phomoidride B) by SET-mediated Fragmentation Chem. Commun. 2002, 814-815
92. Mehta, G.; Kumaran, R. S. A General, Norbornyl Based Approach to Anti-Bredt Alkenes via Sequential RCM-Fragmentation Strategy Chem. Commun. 2002, 1456-1457
93. Baldwin, J. E.; Beyeler, A.; Cox, R. J.; Keats, C.; Pritchard, G. J.; Adlington, R. M.; Watkin, D. J. Reinvestigation of the Dimerisation Process Forming Isoglaucanic Acid Tetrahedron 1999, 55, 7363-7374
94. Baldwin, J. E.; Adlington, R. M.; Roussi, F.; Bulger, P. G.; Marquez, R.; Mayweg, A. V. W. Studies towards the Biomimetic Synthesis of the Nonadrides CP-225,917 and CP263,114 Tetrahedron 2001, 57, 7409-7416
95. Sulikowski, G. A.; Agnelli, F.; Corbett, R. M. Investigations into a Biomimetic Approach toward CP-225,917 and CP-263,114 J. Org. Chem. 2000, 65, 337-342
96. Sulikowski, G. A.; Liu, W.; Agnelli, F.; Corbett, R. M.; Luo, Z.; Hershberger, S. J. Progress toward a Biomimetic Synthesis of Phomoidride B Org. Lett. 2002, 4, 1451-1454
97. Devaux, J. F.; ONeil, S. V.; Guillo, N.; Paquette, L. A. Studies toward an Asymmetric Synthesis of CP-263,114 and CP-225,917 Collect. Czech. Chem. Commun. 2000, 65, 490-510
98. Toyota, M.; Majo, V. J.; Ihara, M. A Facile Synthesis of Bridged Bicycloalkenones from Enol Silanes of Medium and Large Rings by Palladium(II) Mediated Cycloalkenylation Reaction Tetrahedron Lett. 2001, 42, 1555-1558
99. Nicolaou, K. C.; Baran, P. S. The CP Molecule Labyrinth: A Paradigm of How Endeavors in Total Synthesis Lead to Discoveries and Inventions in Organic Synthesis Angew. Chem., Int. Ed. 2002, 41, 2678-2720
100. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogianniakis, G. The Diels-Alder Reaction in Total Synthesis Angew. Chem., Int. Ed. 2002, 41, 1668
101. Nicolaou, K. C.; Jung, J.; Yoon, W. H.; Fong, K. C.; Choi, H.-S.; He, Y.; Zhong, Y.-L.; Baran, P. S. Total Synthesis of the CP-Molecules (CP-263,114 and CP 225,917, Phomoidrides B and A). 1. Racemic and Asymmetric Synthesis of Bicyclo[4.3.1] Key Building Blocks J. Am. Chem. Soc. 2002, 124, 2183-2189
102. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Fong, K. C.; Choi, H.-S. Total Synthesis of the CP-Molecules (CP-263,114 and CP 225,917, Phomoidrides B and A). 2. Model Studies for Construction of Key Structural Elements and First-Generation Strategy J. Am. Chem. Soc. 2002, 124, 2190-2201
103. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S.; Jung, J.; Choi, H.-S.; Yoon, W. H. Total Synthesis of the CP-Molecules (CP-263,114 and CP 225,917, Phomoidrides B and A). 3. Completion and Synthesis of Advanced Analogues J. Am. Chem. Soc. 2002, 124, 2202-2211
104. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. New Synthetic Technology for the Rapid Construction of Novel Heterocycles, Part 1: The Reaction of Dess-Martin Periodinane with Anilides and Related Compounds Angew. Chem., Int. Ed. 2000, 39, 622-625
105. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. New Synthetic Technology for the Rapid Construction of Novel Heterocycles, Part 2. The Reaction of IBX with Anilides and Related Compounds Angew. Chem., Int. Ed. 2000, 39, 625-628
106. Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y.-L.; Sugita, K.; Zou, N. Mechanistic Studies of Periodinane-Mediated Reactions of Anilides and Related Systems Angew. Chem., Int. Ed. 2001, 40, 202-206
107. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Sugita, K. Iodine(V) Reagents in Organic Synthesis. Part 1. Synthesis of Polycyclic Heterocycles via Dess-Martin Periodinane-Mediated Cascade Cyclization: Generality, Scope, and Mechanism of the Reaction J. Am. Chem. Soc. 2002, 124, 2212-2220
108. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.-L. Iodine(V) Reagents in Organic Synthesis. Part 2. Access to Complex Molecular Architectures via Dess-Martin Periodinane-Generated o-Imidoquinones J. Am. Chem. Soc. 2002, 124, 2221-2232
109. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. Iodine(V) Reagents in Organic Synthesis. Part 3. New Routes to Heterocyclic Compounds via o-Iodoxybenzoic Acid-Mediated Cycllizations: Generality, Scope, and Mechanism J. Am. Chem. Soc. 2002, 124, 2233-2244
110. Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. Iodine(V) Reagents in Organic Synthesis. Part 4. o-Iodoxybenzoic Acid as a Chemospecific Tool for Single Electron Transfer-Based Oxidation Processes J. Am. Chem. Soc. 2002, 124, 2245-2258
111. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. A New Method for the One-Step Synthesis of α,β-Unsaturated Carbonyl Systems from Saturated Alcohols and Carbonyl Compounds J. Am. Chem. Soc. 2000, 122, 7596-7597
112. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.-L. New Synthetic Technology for the Construction of N-Containing Quinones and Derivative Thereof: Total Synthesis of Epoxyquinomycin B Angew. Chem., Int. Ed. 2001, 40, 207-210
113. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Novel IBX-Mediated Processes for the Synthesis of Amino Sugars and Libraries Thereof Angew. Chem., Int. Ed. 2000, 39, 2525-2529
114. Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. New Reactions of IBX: Oxidation of Nitrogen- and Sulfur-Containing Substrates to Afford Useful Synthetic Intermediates Angew. Chem., Int. Ed. 2003, 42, 4077-4082
115. 5: Mild and Selective Alternative Reagents to IBX for the Dehydrogenation of Aldehydes and Ketones Angew. Chem., Int. Ed. 2002, 41, 1386-1389
116. Chen, C.; Layton, M. E.; Shair, M. D. Stereospecific Synthesis of the CP-263,114 Core Structure J. Am. Chem. Soc. 1998, 120, 10784-10785
117. Sheehan, S. M.; Lalic, G.; Chen, J. S.; Shair, M. D. A Highly Efficient and Convergent Reaction for the Synthesis of Bridgehead Enone-Containing Polycyclic Ring Systems Angew. Chem., Int. Ed. 2000, 39, 2714-2715
118. Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. Synthesis of (+)-CP-263,114 J. Am. Chem. Soc. 2000, 122, 7424-7425
119. Xu, K.; Lalic, G.; Sheehan, S. M.; Shair, M. D. Dynamic Kinetic Resolution during a Cascade Reaction on Substrates with Chiral All-Carbon Quaternary Centers Angew. Chem., Int. Ed. 2005, 44, 2259-2261
120. Bio, M. M.; Leighton, J. L. An Approach to the Synthesis of CP-263,114: A Remarkably Facile Siloxy-Cope Rearrangement J. Am. Chem. Soc. 1999, 121, 890-891
121. Bio, M. M.; Leighton, J. L. Stereoconvergent Palladium-Catalyzed Carbonylation of both E and Z Isomers of a 2-Trifloxy-1,3-butadiene Org. Lett. 2000, 2, 2905-2907
122. Njardson, J. T.; Wood, J. L. Evolution of a Synthetic Approach to CP-263,114 Org. Lett. 2001, 3, 2431-2434
123. Njardson, J. T.; McDonald, I. M.; Spiegel, D. A.; Inoue, M.; Wood, J. L. An Expeditious Approach toward the Total Synthesis of CP-263,114 Org. Lett. 2001, 3, 2435-2438
124. Barton, D. H. R.; Parekh, S. I.; Tse, C.-L. On the Stability and Radical Deoxygenation of Tertiary Xanthates Tetrahedron Lett. 1993, 34, 2733-2736
125. Barton, D. H. R.; McCombie, S. W. A New Method for the Deoxygenation of Secondary Alcohols J. Chem. Soc., Perkin Trans. 1 1975, 16, 1574-1585
126. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. On the Mechanism of Deoxygenation of Secondary Alcohols by Tin Hydride Reduction of Methyl Xanthates and Other Thiocarbonyl Derivatives Tetrahedron Lett. 1990, 31, 3991-3994
127. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. Deoxygenation of Alcohols Employing Water as the Hydrogen Atom Source J. Am. Chem. Soc. 2005, 127, 12513-12515
128. Ruscic, B.; Wagner, A. F.; Harding, L. B.; Asher, R. L.; Feller, D.; Dixon, D. A.; Peterson, K. A.; Song, Y.; Qian, X.; Ng, C.-Y.; Liu, J.; Chen, W.; Schwenke, D. W. On the Enthalpy of Formation of Hydroxyl Radical and Gas-Phase Bond Dissociation Energies of Water and Hydroxyl J. Phys. Chem. A 2002, 106, 2727-2747
129. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. The C-H Bond Energy of Benzene J. Am. Chem. Soc. 1995, 117, 2590-2599
130. Medeiros, M. R.; Schacherer, L. N.; Spiegel, D. A.; Wood, J. L. Expanding the Scope of Trialkylborane/Water-Mediated Radical Reactions Org. Lett. 2007, 9, 4427-4429
131. Rapoport, H.; Holden, K. G. The Synthesis of Prodigiosin J. Am. Chem. Soc. 1962, 84, 635-642
132. Fürstner, A. Chemistry and Biology of Roseophilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years Angew. Chem., Int. Ed. 2003, 42, 3582-3603
133. Trost, B. M.; Trost, M. K. Intramolecular Enyne Methathesis Reaction. Route to Bridged Bicycles with Bridgehead Olefins J. Am. Chem. Soc. 1991, 113, 1850-1852
134. Trost, B. M.; Chang, V. K. An Approach to Botrydianes: On the Steric Demands of a Metal Catalyzed Enyne Metathesis Synthesis 1993, 824-832
135. HFB-Catalyzed Metathesis of 1,6-Enyne: Evidence of the Alkylidenepalladium Intermediates Angew. Chem., Int. Ed. Engl. 1993, 32, 1085-1087
136. Trost, B. M.; Yanai, M.; Hoogsteen, K. A Palladium-Catalyzed [2 + 2] Cycloaddition: Mechanism of a Pd-Catalyzed Enyne Metathesis J. Am. Chem. Soc. 1993, 115, 5294-5295
137. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. Platinum- and Acid-Catalyzed Enyne Metathesis Reactions: Mechanistic Studies and Applications to the Syntheses of Streptorubin B and Metacycloprodigiosin J. Am. Chem. Soc. 1998, 120, 8305-8314
138. 2-Catalyzed Conversion of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes: Anomalous Bond Connection in Skeletal Reorganization of Enynes Organometallics 1996, 15, 901-903
139. 2 J. Am. Chem. Soc. 2000, 122, 6785-6786
140. Fürstner, A.; Stelzer, F.; Szillat, H. Platinum-Catalyzed Cycloisomerization Reactions of Enynes J. Am. Chem. Soc. 2001, 123, 11863-11869
141. 2-Catalyzed Cycloisomerization Reaction J. Org. Chem. 2002, 67, 6264-6267
142. Qian-Cutrone, J.; Huang, S.; Shu, Y.-Z.; Vyas, D.; Fairchild, C.; Menendez, A.; Krampitz, K.; Dalterio, R.; Klohr, S. E.; Gao, Q. Stephacidin A and B: Two Structurally Novel, Selective Inhibitors of the Testosterone-Dependent Prostate LNCaP Cells J. Am. Chem. Soc. 2002, 124, 14556-14557
143. Fenical, W.; Jensen, P.; Cheng, X. C. Avrainvillamide, a Cytotoxic Marine Natural Product, and the Derivatives Thereof. U.S. Patent 6,066,635, 2000.
144. Luzung, M. R.; Lewis, C. A.; Baran, P. S. Direct, Chemoselective N-tert-Prenylation of Indoles by C-H Functionalization Angew. Chem., Int. Ed. 2009, 48, 7025-7029
145. Li, S.-M. Prenylated Indole Derivatives from Fungi: Structure Diversity, Biological Activities, Biosynthesis and Chemoenzymatic Synthesis Nat. Prod. Rep. 2010, 27, 57
146. Steinhardt, S. E.; Silverston, J. S.; Vanderwal, C. D. Stereocontrolled Synthesis of Z-Dienes via an Unexpected Pericyclic Cascade Rearrangement of 5-Amino-2,4-pentadienals J. Am. Chem. Soc. 2008, 130, 7560-7561
147. Hafner, K.; Asmus, K.-D. Zur Kenntnis der Azulene, XIV. Darstellung substituierter Glutacondialdehyd-Derivate und ihre Überführung in Azulene Liebigs Ann. Chem. 1964, 671, 31-40
148. Kearny, A. M.; Vanderwal, C. D. Synthesis of Nitrogen Heterocycles by the Ring Opening of Pyridinium Salts Angew. Chem., Int. Ed. 2006, 45, 7803-7806
149. Steinhardt, S. E.; Vanderwal, C. D. Complex Polycyclic Lactams from Pericyclic Cascade Reactions of Zincke Aldehydes J. Am. Chem. Soc. 2009, 131, 7546-7547
150. Ersmark, K.; Del Valle, J. R.; Hanessian, S. Chemistry and Biology of the Aeruginosin Family of Serine Protease Inhibitors Angew. Chem., Int. Ed. 2008, 47, 1202-1223
151. Welker, M.; Von Döhren, H. Cyanobaterial Peptides: Natures Own Combinatorial Biosynthesis FEMS Microbiol. Rev. 2006, 30, 530-563
152. Fuji, K.; Sivonen, K.; Adachi, K.; Noguchi, K.; Shimizu, Y.; Sano, H.; Hirayama, K.; Suzuki, M.; Harada, K. Comparative Study of Toxic and Non-toxic Cyanobacterial Products: A Novel Glycoside, Suomilide, from Non-toxic Nodularia spumigena HKVV Tetrahedron Lett. 1997, 38, 5529-5532
153. Pluotno, A.; Carmeli, S. Banyasin A and Banyasides A and B, Three Novel Modified Peptides from a Water Bloom of the Cyanobacterium Nostoc sp Tetrahedron 2005, 61, 575-583
154. Schindler, C. S.; Stephenson, C. R. J.; Carreira, E. M. Enantioselective Synthesis of the Core of Banyaside, Suomilide, and Spumigin HKVV Angew. Chem., Int. Ed. 2008, 47, 8852-8855
155. Schindler, C. S.; Bertschi, L.; Carreira, E. M. Total Synthesis of Nominal Banyaside B: Structural Revision of the Glycosylation Site Angew. Chem., Int. Ed. 2010, 49, 9229-9232
156. Oliver, J. S.; Oyelere, A. Aminoacylation of Nucleosides with FMOC Amino Acid Fluorides J. Org. Chem. 1996, 61, 4168-4171
157. Schindler, C. S.; Forster, P. M.; Carreira, E. M. Facile Formation of N-Acyl-oxazolidinone Derivatives Using Acid Fluorides Org. Lett. 2010, 12, 4102-4105
158. Ager, D. J.; Prakash, I.; Schaad, D. R. 1,2-Amino Alchols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis Chem. Rev. 1996, 96, 835-876
159. Evans, D. A.; Bartoli, J.; Shih, T. L. Enantioselective Aldol Condensations. 2. Erythro-selective Chiral Aldol Condensations via Boron Enolates J. Am. Chem. Soc. 1981, 103, 2127-2129
160. Gage, J. R.; Evans, D. A. Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S∗,3S∗)-3-Hydroxy-3-phenyl-2-methylpropanoic Acid Org. Synth. 1990, 68, 83-87
161. Davies, S. G.; Doisneau, G. J.-M. Base Induced C-5 Epimerisation of 4-Methyl-5-phenyl Oxazolidinones: Chiral Auxiliaries Derived from Norephedrine and Norpseudoephedrine Tetrahedron: Asymmetry 1993, 4, 2513-2516
162. Ager, D. J.; Allen, D. R.; Schaad, D. R. Simple and Efficient N-Acylation Reactions of Oxazolidine Auxiliaries Synthesis 1996, 1283-1285
163. Schindler, C. S.; Diethelm, S.; Carreira, E. M. Nucleophilic Opening of Oxabicyclic Ring Systems Angew. Chem., Int. Ed. 2009, 48, 6296-6299
164. Schindler, C. S.; Carreira, E. M. Rapid Formation of Complexity in the Total Synthesis of Natural Products Enabled by Oxabicyclo[2.2.1]heptene Building Blocks Chem. Soc. Rev. 2009, 38, 3222-3241
165. Diethelm, S.; Schindler, C. S.; Carreira, E. M. Synthesis of Microcin SF608 through Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane Org. Lett. 2010, 12, 3950-3953
166. Diethelm, S.; Schindler, C. S.; Carreira, E. M. Acess to the Aeruginosin Serine Protease Inhibitors through the Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane: Total Synthesis of Microcin SF608 Chem. - Eur. J. 2014, 20, 6071-6080
167. Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, T.; Hirota, H. Gambieric Acids: Unprecedented Potent Antifungal Substances Isolated from Cultures of a Marine Dinoflagellate Gambierdiscus toxicus J. Am. Chem. Soc. 1992, 114, 1102-1103
168. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. Gambieric Acids, New Potent Antifungal Substances with Unprecedented Polyether Structures from a Marine Dinoflagellate Gambierdiscus toxicus J. Org. Chem. 1992, 57, 5448-5453
169. Inoue, M.; Hirama, M.; Satake, M.; Sugiyama, K.; Yasumoto, T. Inhibition of Brevetoxin Binding to the Voltage-Gated Sodium Channel by Gambierol and Gambieric Acid-A Toxicon 2003, 41, 469-474
170. Roberts, S. W.; Rainier, J. D. Synthesis of an A-E Gambieric Acid Subunit with Use of a C-Glycoside Centered Strategy Org. Lett. 2007, 9, 2227-2230
171. Rainier, J. D.; Allwein, S. P.; Cox, J. M. C-Glycosides to Fused Polycyclic Ethers. A Formal Synthesis of (±)-Hemibrevetoxin B J. Org. Chem. 2001, 66, 1380-1386
172. 4-Zn Systems by Addition of Lead J. Org. Chem. 1994, 59, 2668-2670
173. Majumder, U.; Rainier, J. D. Olefinic-Ester Cyclizations Using Takai-Utimoto Reduced Titanium Alkylidenes Tetrahedron Lett. 2005, 46, 7209-7211
174. Iyer, K.; Rainier, J. D. Olefinic Ester and Diene Ring-Closing Metathesis Using a Reduced Titanium Alkylidene J. Am. Chem. Soc. 2007, 129, 12604-12605
175. Zhou, J.; Rainier, J. D. Olefinic-Amide and Olefinic-Lactam Cyclizations Org. Lett. 2009, 11, 3774-3776
176. Garrido, L.; Zubía, E.; Ortega, M. J.; Salvá, J. Haouamines A and B: A New Class of Alkaloids from the Ascidian Aplidium haouarianum J. Org. Chem. 2003, 68, 293-299
177. Grundl, M. A.; Trauner, D. Synthetic Studies toward the Haouamines Org. Lett. 2006, 8, 23-25
178. Grundl, M. A.; Kaster, A.; Beaulieu, E. D.; Trauner, D. Development of a Friedel-Crafts Triflation Org. Lett. 2006, 8, 5429-5432
179. Baran, P. S.; Burns, N. Z. Total Synthesis of (±)-Haouamine A J. Am. Chem. Soc. 2006, 128, 3908-3909
180. Gravel, E.; Poupon, E.; Hocquemiller, R. Retracted Article: Biogenic Hypothesis and First Steps towards a Biomimetic Synthesis of Haouamines Chem. Commun. 2007, 719-721
181. Chichibabin, A. E. Synthesis of Pyridine Bases from Saturated Aldehydes and Ammonia J. Russ. Phys. Chem. Soc. 1905, 37, 1229
182. Yu, L.-B.; Chen, D.; Li, J.; Ramirez, J.; Wang, P. G.; Bott, S. G. Lanthanide-Promoted Reactions of Aldehydes and Amine Hydrochlorides in Aqueous Solution: Synthesis of 2,3-Dihydropyridinium and Pyridinium Derivatives J. Org. Chem. 1997, 62, 208-211
183. Burns, N. Z.; Baran, P. S. On the Origin of the Haouamine Alkaloids Angew. Chem., Int. Ed. 2008, 47, 205-208
184. Saalfrank, R. W.; Reihs, S.; Hug, M. Aerobic Oxygenation/Dehydrogenation of Olefins and 1,4-Dihydropyridines Catalyzed by Tris(tetrazolyl enolate)iron(III) Complexes Tetrahedron Lett. 1993, 34, 6033-6036
185. Eliel, E. L.; McBride, R. T.; Kaufmann, S. Abnormal Chichibabin Reactions: The Condensation of Phenylacetaldehyde and Homoveratric Aldehyde with Ammonia J. Am. Chem. Soc. 1953, 75, 4291-4296
186. Komoda, T.; Sugiyama, Y.; Abe, N.; Imachi, M.; Hirota, H.; Hirota, A. Tetrapetalone A, a Novel Lipoxygenase Inhibitor from Streptomyces sp Tetrahedron Lett. 2003, 44, 1659-1661
187. Komoda, T.; Sugiyama, Y.; Abe, N.; Imachi, M.; Hirota, H.; Koshino, H.; Hirota, A. Revised structure of tetrapetalone A and its absolute stereochemistry Tetrahedron Lett. 2003, 44, 7417-7419
188. Komoda, T.; Yoshida, K.; Abe, N.; Sugiyama, Y.; Imachi, M.; Hirota, H.; Koshino, H.; Hirota, A. Tetrapetalone A, a Novel Lipoxygenase Inhibitor from Streptomyces sp Biosci. Biotechnol. Biochem. 2004, 68, 104-111
189. Carlsen, P. N.; Mann, T. J.; Hoveyda, A. H.; Frontier, A. J. Synthesis of (±)-Tetrapetalone A-Me Aglycon Angew. Chem., Int. Ed. 2014, 53, 9334-9338
190. Jiang, C.; Frontier, A. J. Stereoselective Synthesis of Pyrrolidine Derivatives via Reduction of Substituted Pyrroles Org. Lett. 2007, 9, 4939-4942
191. Donohoe, T. J.; Headley, C. E.; Cousins, R. P. S.; Cowley, A. Flexibility in the Partial Reduction of 2,5-Disubstituted Pyrroles: Application to the Synthesis of DMDP Org. Lett. 2003, 5, 999-1002
192. Naya, Y.; Kotake, M. New Monoterpenoids from Hop Oil Tetrahedron Lett. 1968, 9, 1645-1649
193. Warmers, U.; Koenig, W. A. Sesquiterpene Constituents of the Liverwort Bazzania trilobata Phytochemistry 1999, 52, 99-104
194. Rudi, A.; Kashman, Y. Chelodane, Barekoxide, and Zaatirin: Three New Diterpenoids from the Marine Sponge Chelonaplysilla erecta J. Nat. Prod. 1992, 55, 1408-1414
195. Justicia, J.; Oller-López, J. L.; Campana, A. G.; Oltra, E.; Cuerva, J. M.; Bunuel, E.; Cárdenas, D. J. 7-endo Radical Cyclizations Catalyzed by Titanocene(III): Straightforward Synthesis of Terpenoids with Seven-Membered Carbocycles J. Am. Chem. Soc. 2005, 127, 14911-14921
196. 2O Org. Lett. 2006, 8, 5433-5436
197. Enemærke, R. J.; Larsen, J.; Hjøllund, G. T.; Skrydstrup, T.; Dassbjerg, K. Influence of the Halogen in Titanocene Halide Promoted Reductions Organometallics 2005, 24, 1252-1262
198. Dunlap, M. S.; Nicholas, K. M. Catalyst Structural Effects in Titanocene-Catalyzed Pinacol Coupling: Activity, Stereoselectivity and Mechanistic Implications J. Organomet. Chem. 2001, 630, 125-131
199. Gansäuer, A.; Bauer, D. Novel Concept for Efficient Transition-Metal-Catalyzed Reactions: A Highly Diastereoselective Titanocene-Catalyzed Pinacol Coupling under Buffered Protic Conditions J. Org. Chem. 1998, 63, 2070-2071
200. Gansäuer, A. Pinacol Coupling of Aromatic Aldehydes Catalysed by a Titanocene Complex: A Transition Metal Catalysed Radical Reaction Chem. Commun. 1997, 457-458
201. Handa, Y.; Inanaga, J. A Highly Stereoselective Pinacolization of Aromatic and α,β-Unsaturated Aldehydes Mediated by Titanium(III)-Magnesium(II) Complex Tetrahedron Lett. 1987, 28, 5717-5718
202. Oller-López, J. L.; Campana, A. G.; Cuerva, J. M.; Oltra, J. E. Aromatic Carbonyl Compound Reduction and Pinacol Coupling Process Mediated by Titanocene(III)/Zn in Water Synthesis 2005, 2619-2622
203. Molander, G. A. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 165.
204. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. Isolation and Structure Determination of Diazonamides A and B, Unusual Cytotoxic Metabolites from the Marine Ascidian Diazona chinensis J. Am. Chem. Soc. 1991, 113, 2303-2304
205. Cruz-Monserrate, Z.; Vervoort, H. C.; Bai, R.; Newman, D. J.; Howell, S. B.; Los, G.; Mullaney, J. T.; Williams, M. D.; Pettit, G. R.; Fenical, W.; Hamel, E. Diazonamide A and a Synthetic Structural Analog: Disruptive Effects on Mitosis and Cellular Microtubules and Analysis of Their Interactions with Tubulin Mol. Pharmacol. 2003, 63, 1273-1280
206. Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Total Synthesis of Nominal Diazonamides, Part 1: Convergent Preparation of the Structure Proposed for (-)-Diazonamide A Angew. Chem., Int. Ed. 2001, 40, 4765-4769
207. Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Total Synthesis of Nominal Diazonamides, Part 2: On the True Structure and Origin of Natural Isolates Angew. Chem., Int. Ed. 2001, 40, 4770-4773
208. Wang, G.; Shang, L.; Burgett, A. W. G.; Harran, P. G.; Wang, X. Diazonamide Toxins Reveal an Unexpected Function for Ornithine δ-Amino Transferase in Mitotic Cell Division Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 2068-2073
209. Nicolaou, K. C.; Bella, B.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Snyder, S. A. Total Synthesis of Diazonamide A Angew. Chem. 2002, 114, 3645-3649
210. Nicolaou, K. C.; Bella, B.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Snyder, S. A. Total Synthesis of Diazonamide A Angew. Chem., Int. Ed. 2002, 41, 3495-3499
211. Nicolaou, K. C.; Koumbis, A. E.; Snyder, S. A.; Simonsen, K. B. Novel Reactions Initiated by Titanocene Methylidenes: Deoxygenation of Sulfoxides, N-Oxides, and Selenoxides Angew. Chem., Int. Ed. 2000, 39, 2529-2533
212. Carroll, A. R.; Hyde, E.; Smith, J.; Quinn, R. G.; Guymer, G.; Forster, P. I. Actinophyllic Acid, a Potent Indole Alkaloid Inhibitor of the Coupled Enzyme Assay Carboxypeptidase U/Hippuricase from the Leaves of Alstonia actinophylla (Apocynaceae) J. Org. Chem. 2005, 70, 1096-1099
213. Willemse, J. L.; Hendricks, D. F. Measurement of Procarboxypeptidase U (TAFI) in Human Plasma: A Laboratory Challenge Clin. Chem. 2006, 52, 30-36
214. Dubis, J.; Witkiewics, W. The Role of Thrombin-Activatible Fibrinolysis Inhibitor in the Pathophysiology of Hemostasis Adv. Clin. Exp. Med. 2010, 19, 379-387
215. Beatty, J. W.; Stephenson, C. R. J. Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis Acc. Chem. Res. 2015, 48, 1474-1484
216. Fukuzumi, S.; Mochizuku, S.; Tanaka, T. Photocatalytic Reduction of Phenacyl Halides by 9,10-Dihydro-10-methylacridine: Control between the Reductive and Oxidative Quenching Pathways of Tris(bipyridine)ruthenium Complex Utilizing an Acid Catalysis J. Phys. Chem. 1990, 94, 722-726
217. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Electron-Transfer Photoredox Catalysis: Development of a Tin-free Reductive Dehalogenation Reaction J. Am. Chem. Soc. 2009, 131, 8756-8757
218. Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Electron-Transfer Photoredox Catalysis: Intramolecular Radical Addition to Indoles and Pyrroles Org. Lett. 2010, 12, 368-371
219. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Visible-Light Photoredox Catalysis in Flow Angew. Chem., Int. Ed. 2012, 51, 4144-4147
220. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts J. Am. Chem. Soc. 2011, 133, 4160-4163
221. Dai, C.; Narayanam, C. D.; Stephenson, C. R. J. Visible-Light-Mediated Conversion of Alcohols to Halides Nat. Chem. 2011, 3, 140-145
222. Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. Photoredox Catalysis in a Complex Pharmaceutical Setting: Toward the Preparation of JAK2 Inhibitor LY2784544 J. Org. Chem. 2014, 79, 11631-11643
223. Beatty, J. W.; Stephenson, C. R. J. Synthesis of (-)-Pseudotabersonine, (-)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow J. Am. Chem. Soc. 2014, 136, 10270-10273
224. Crooks, P. A.; Robinson, B. The Isolation and Identification of Quininone from Cinchona ledgeriana J. Pharm. Pharmacol. 1970, 22, 469-470
225. Wan, Y.-P.; Porter, T. H.; Folkers, K. Antimalarial Quinones for Prophylaxis Based on a Rationale of Inhibition of Electron Transfer in Plasmodium Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 952-956
226. Zhang, X.; Larock, R. C. Synthesis of Spiro[4.5]trienones by Intramolecular ipso-Halocyclization of 4-(p-Methoxyaryl)-1-alkynes J. Am. Chem. Soc. 2005, 127, 12230-12231
227. Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Synthesis of Substituted Quinolines by Electrophilic Cyclization of N-(2-Alkynyl)anilines Org. Lett. 2005, 7, 763-766
228. Morita, H.; Ishioka, N.; Takatsu, H.; Iizuka, T.; Kobayashi, J. Daphmanidins E and F, Alkaloids from Daphniphyllum teijmannii J. Nat. Prod. 2006, 69, 418-420
229. Weiss, M. E.; Carreira, E. M. Total Synthesis of (+)-Daphmanidin E Angew. Chem., Int. Ed. 2011, 50, 11501-11505
230. Weiss, M. E.; Kreis, L. M.; Lauber, A.; Carreira, E. M. Cobalt-Catalyzed Coupling of Alkyl Iodides with Alkenes: Deprotonation of Hydridocobalt Enables Turnover Angew. Chem., Int. Ed. 2011, 50, 11125-11128
231. Grabley, S.; Kretzschmar, G.; Mayer, M.; Phillips, S.; Thiericke, R.; Wink, J.; Zeeck, A. Secondary Metabolites by Chemical Screening, 24. Oasomycins, New Macrolactones of the Desertomycyin Family Liebigs Ann. Chem. 1993, 573-579
232. Evans, D. A.; Nagorny, P.; McRae, K. J.; Reynolds, D. J.; Sonntag, L.-S.; Vounatsos, F.; Xu, R. Enantioselective Synthesis of Oasomycin A, Part I: Synthesis of the C1-C12 and C13-C28 Subunits Angew. Chem., Int. Ed. 2007, 46, 475-639
233. Evans, D. A.; Nagorny, P.; Reynolds, D. J.; McRae, K. J. Enantioselective Synthesis of Oasomycin A, Part II: Synthesis of the C29-C46 Subunit Angew. Chem., Int. Ed. 2007, 46, 541-544
234. Evans, D. A.; Nagorny, P.; McRae, K. J.; Sonntag, L.-S.; Reynolds, D. J.; Vounatsos, F. Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure Angew. Chem., Int. Ed. 2007, 46, 545-548
235. Kobayashi, Y.; Tan, S.-H.; Kishi, Y. Toward Creation of a Universal NMR Database for Stereochemical Assignment: Complete Structure of the Desertomycin/Oasomycin Class of Natural Products J. Am. Chem. Soc. 2001, 123, 2076-2078
236. Evans, D. A.; Nagorny, P.; Xu, R. Ceric Ammonium Nitrate Promoted Oxidation of Oxazoles Org. Lett. 2006, 8, 5669-5671
237. Kiat, T. S.; Pippen, R.; Yusof, R.; Ibrahim, H.; Khalid, N.; Rahman, N. A. Inhibitory Activity of Cyclohexenyl Chalcone Derivatives and Flavonoids of Fingerroot, Boesenbergia rotunda (L.), towards Dengue-2 Virus NS3 Protease Bioorg. Med. Chem. Lett. 2006, 16, 3337-3340
238. Nomura, T. The Chemistry and Biosynthesis of Isoprenylated Flavonoids from Moraceous Plants Pure Appl. Chem. 1999, 71, 1115-1118
239. Majetich, G.; Zhang, Y. Concise Synthesis of (±)-Perovskone J. Am. Chem. Soc. 1994, 116, 4979-4980
240. Cong, H.; Ledbetter, G.; Rowe, G. T.; Caradonna, J. P.; Porco, J. A., Jr. Electron Transfer-Initiated Diels-Alder Cycloadditions of 2′-Hydroxychalcones J. Am. Chem. Soc. 2008, 130, 9214-9215
241. Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco, J. A., Jr. Silver Nanoparticle-Catalyzed Diels-Alder Cycloadditions of 2′-Hydroxychalcones J. Am. Chem. Soc. 2010, 132, 7514-7518
242. Urban, S.; Leone, P. A.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. Axinellamines A-D, Novel Imidazo-Azolo-Imidazole Alkaloids from the Australian Marine Sponge Axinella sp J. Org. Chem. 1999, 64, 731-735
243. OMalley, D. P.; Yamaguchi, J.; Young, I. S.; Seiple, I. B.; Baran, P. S. Total Synthesis of (±)-Axinellamines A and B Angew. Chem., Int. Ed. 2008, 47, 3581-3583
244. Rodriquez, R. A.; Steed, D. B.; Kawamata, Y.; Su, S.; Smith, P. A.; Steed, T. C.; Romesburg, F. E.; Baran, P. S. Axinellamines as Broad-Spectrum Antibacterial Agents: Scalable Synthesis and Biology J. Am. Chem. Soc. 2014, 136, 15403-15413
245. Su, S.; Rodriguez, R. A.; Baran, P. S. Scalable, Stereocontrolled Total Syntheses of (±)-Axinellamines A and B J. Am. Chem. Soc. 2011, 133, 13922-13925
246. Rodriguez, R. A.; Pan, C.-M.; Yabe, Y.; Kawamata, Y.; Eastgate, M. D.; Baran, P. S. Palauchlor: A Practical and Reactive Chlorinating Reagent J. Am. Chem. Soc. 2014, 136, 6908-6911
247. Mulder, J. G.; Diepenhorst, P.; Plieger, P.; Bruggermann-Togans, I. E. M. Hatching agent for the potato cyst nematode. World Patent WO1993002083 A1, 1993, (Chem. Abstr. 118, 185844z).
248. Tanino, K.; Takahashi, M.; Tomata, Y.; Tokura, H.; Uehara, T.; Narabu, T.; Miyashita, M. Total Synthesis of Solanoeclepin A Nat. Chem. 2011, 3, 484-488
249. Ndungu, J. M.; Larson, K. K.; Sarpong, R. Development of an Anomalous Heck Reaction: Skeletal Rearrangement of Divinyl and Enyne Carbinols Org. Lett. 2005, 7, 5845-5848
250. Kobayashi, J.; Suzuki, H.; Shimbo, K.; Takeya, K.; Morita, H. Celogentins A-C, New Antimitotic Bicyclic Peptides from the Seeds of Celosia argentea J. Org. Chem. 2001, 66, 6626-6633
251. Chan, K.-S.; Koh, C.-G.; Li, H. Y. Mitosis-Targeted Anti-cancer Therapies: Where They Stand Cell Death Dis. 2012, 3 e411
252. Suzuki, J.; Morita, H.; Iwasaki, S.; Kobayashi, J. New Antimitotic Bicyclic Peptides, Celogentins D-H and J, from the Seeds of Celosia argentea Tetrahedron 2003, 59, 5307
253. He, L.; Yang, L.; Castle, S. L. Synthesis of the Celogentin C Right-Hand Ring Org. Lett. 2006, 8, 1165-1168
254. Ma, B.; Litvinov, D. N.; He, L.; Banerjee, B.; Castle, S. L. Total Synthesis of Celogentin C Angew. Chem., Int. Ed. 2009, 48, 6104-6107
255. Ma, B.; Banerjee, B.; Litvinov, D.; He, L.; Castle, S. L. Total Synthesis of the Antimitotic Bicyclic Peptide Celogentin C J. Am. Chem. Soc. 2010, 132, 1159-1171
256. Sato, B.; Muramatsu, H.; Miyauchi, M.; Hori, Y.; Takase, S.; Hino, M.; Hashimoto, S.; Terano, H. A New Antimitotic Substance, FR182877 J. Antibiot. 2000, 53, 123-130
257. Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Postulated Biogenesis of WS9885B and Progress toward and Enantioselective Synthesis Org. Lett. 1999, 1, 645-648
258. Vanderwal, C. D.; Vosburg, D. A.; Sorensen, E. J. Intramolecular Allenolate Acylations in Studies toward a Synthesis of FR182877 Org. Lett. 2001, 3, 4307-4310
259. Mohr, J. T.; Ebner, D. C.; Stoltz, B. M. Catalytic Enantioselective Stereoablative Reactions: An Unexploited Approach to Enantioselective Catalysis Org. Biomol. Chem. 2007, 5, 3571-3576
260. Daranas, A. H.; Fernández, J. J.; Gavín, J. A.; Norte, M. New Alkaloids from a Marine Zoanthid Tetrahedron 1999, 55, 5539-5546
261. Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. The Biology and Chemistry of the Zoanthamine Alkaloids Angew. Chem., Int. Ed. 2008, 47, 2365-2386
262. Villar, R. M.; Gil-Longo, J.; Daranas, A. H.; Souto, M. L.; Fernández, J. J.; Peixinho, S.; Barral, M. A.; Santafé, G.; Rodríguez, J.; Jiménez, C. Evaluation of the Effects of Several Zoanthamine-type Alkaloids on the Aggregation of Human Platelets Bioorg. Med. Chem. 2003, 11, 2301-2306
263. Stockdill, J. L.; Behenna, D. C.; Stoltz, B. M. Unexpected Decarbonylation during an Acid-Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol Tetrahedron Lett. 2009, 50, 3182-3184
264. Elovson, J.; Vagelos, P. R. Structure of the Major Species of Chlorosulfolipid from Ochromonas danica: 2,2,11,13,15,16-Hexachloro-N-docosane 1,14-Disulfate Biochemistry 1970, 9, 3110-3126
265. Nilewski, C.; Geisser, R. W.; Carreira, E. M. Total Synthesis of a Chlorosulfolipid Cytotoxin Associated with Seafood Poisoning Nature 2009, 457, 573-576
266. Nilewski, C.; Deprez, N. R.; Fessard, T. C.; Li, D. B.; Geisser, R. W.; Carreira, E. M. Synthesis of Undecachlorosulfolipid A: Re-evaluation of the Nominal Structure Angew. Chem., Int. Ed. 2011, 50, 7940-7943
267. Nilewski, C.; Carreira, E. M. Recent Advances in the Total Synthesis of Chlorosulfolipids Eur. J. Org. Chem. 2012, 9, 1685-1698
268. Uemura, D.; Takahashi, K.; Yamamoto, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. Norhalichondrin A: An Antitumor Polyether Macrolide from a Marine Sponge J. Am. Chem. Soc. 1985, 107, 4796-4798
269. Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. Total Synthesis of Halichondrin B and Norhalichondrin B J. Am. Chem. Soc. 1992, 114, 3162-3164
270. Henderson, J. A.; Jackson, K. L.; Phillips, A. J. Highly Functionalized Pyranopyrans from Furans: A Synthesis of the C27-38 and C44-53 Subunits of Norhalichondrin B Org. Lett. 2007, 9, 5299-5302
271. Um, J. M.; Houk, K. N.; Phillips, A. J. Origin of the Stereoselectivity in the Reduction of a Planar Oxacarbenium Org. Lett. 2008, 10, 3769-3772