Recent applications and developments of organic azides in total synthesis of natural products

Natural Product Communications

Volumn 8, Issue 7, 2013, Pages 1021-1034

  Tanimoto, Hiroki ^a   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

1 3 dipolar cycloaddition; Alkaloids; Curtius rearrangement; Organic azides; Schmidt reaction; Staudinger aza wittig reaction; Total synthesis

Indexed keywords

ALKALOID; ALKENE DERIVATIVE; AMATHASPIRAMIDE DERIVATIVE; AZIDE; BALANOL; CALLIPELTOSIDE B; CICINDELOINE; DIHYDRONARCICLASINE; FR 901483; KALIHINOL DERIVATIVE; KEALIININE DERIVATIVE; MELOSCINE; NAAMIDINE H; NAAMINE G; NATURAL PRODUCT; NITRENE; PACAMYCIN; PACTAMYCATE; STENIMONA ALKALOID; UCS 1025A; UNCLASSIFIED DRUG;

AZIDO MICHAEL ADDITION; CHEMICAL REACTION; CURTIUS REARRANGEMENT; CYCLOADDITION; DECOMPOSITION; DIELS ALDER REACTION; DRUG SYNTHESIS; NONHUMAN; PRINS REACTION; REDUCTION; REVIEW; SCHMIDT REACTION; STAUDINGER REACTION; SYNTHESIS; WITTIG REACTION;

EID: 84880765463     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1300800730     Document Type: Review

References (105)

1. Bräse S, Banert K. (2010) Organic Azides, Syntheses and Applications. John Wiley & Sons: Ltd., Chichester, West Susssex, UK.
2. Bräse S, Gil C, Knepper K, Zimmermann V. (2005) Organic azides: and exploding diversity of a unique class of compounds. Angewandte Chemie International Edition, 44, 5188-5240. (Pubitemid 41223873)
3. Cultius T. (1890) Ueber Stickstoffwasserstoffsäure (Azoimid) N3H. Berichte der deutschen chemischen Gesellschaft, 23, 3023-3033.
4. Conrow RE, Dean WD. (2008) Diazidomethane explosion. Organic Process Research & Development. 12, 1285-1286. And also chapter 1 of ref [1], chapter 2 of ref [2], and experimental section of ref [6].
5. Wrobleski A, Coombs TC, Huh CW, Li, S-W, Aubé J. (2012) The Schmidt reaction. Organic Reactions, 78, 1-320.
6. Chiba S. (2012) Application of organic azides for the synthesis of nitrogen-containing molecules. Synlett, 23, 21-44.
7. Nair V, Suja, TD. (2007) Intramolecular 1, 3-dipolar cycloaddition reactions in targeted syntheses. Tetrahedron, 63, 12247-12275. (Pubitemid 350017829)
8. Lang S, Murphy JA. (2006) Azide rearrangements in electron-deficient systems. Chemical Society Reviews, 35, 146-156. (Pubitemid 43485005)
9. Choi J-H, Fushimi K, Abe N, Tanaka H, Maeda S, Morita M, Hara M, Motohashi R, Matsunaga J, Eguchi Y, Ishigaki N, Hashizume D, Koshino H, Kawagishi H. (2010) Disclosure of the "Fairy" of Fairy-Ring-Forming Fungus Lepista sordida. ChemBioChem, 11, 1373-1377.
10. Omura S, Tomoda H, Xu QM, Takahashi Y, Iwai Y. (1986) Triacsins, new inhibitors of acyl-CoA synthetase produced by Streptomyces sp. The Journal of Antibiotics, 39, 1211-1218. (Pubitemid 16013889)
11. Huisgen R. (1963) 1, 3-Dipolar cycloadditions. Past and future. Angewandte Chemie International Edition in English, 2, 565-598.
12. Wong C-H, Zimmerman SC. (2013) Orthogonality in organic, polymer, and supramolecular chemistry: from Merrifield to click chemistry. Chemical Communications, 49, 1679-1695.
13. Kolb HC, Finn MG, Sharpless KB. (2001) Click chemistry: diverse chemical function from a few good reactions. Angewandte Chemie International Edition, 40, 2004-2021.
14. Tornøe, CW, Christensen C, Meldal M. (2002) Peptidotriazoles on solid phase: [1, 2, 3]-triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. The Journal of Organic Chemistry, 67, 3057-3064. (Pubitemid 34457265)
15. Meldal M, Tornøe, CW. (2008) Cu-catalyzed azide-alkyne cycloaddition. Chemical Reviews, 108, 2952-3015.
16. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angewandte Chemie International Edition, 41, 2596-2599. (Pubitemid 34803480)
17. Wu P, Fokin VV. (2007) Catalytic azide-alkyne cycloaddition: Reactivity and applications. Aldrichimica Acta, 40, 7-17.
18. Scriven EFV, Turnbull K. (1988) Azides: Their preparation and synthetic uses. Chemical Reviews. 88, 297-368.
19. Shioiri T, Ninomiya K, Yamada S. (1972) Diphenylphosphoryl azide. New convenient reagent for a modified Curtius reaction and for peptide synthesis. Journal of the American Chemical Society, 94, 6203-6205.
20. Shioiri T. (2007) Diphenyl phosphorazidate (DPPA)-more than three decades later. TCI MAIL, 134, 2-19.
21. Mitsunobu O. (1981) The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis, 1-29.
22. Viaud MC, Rollin P. (1990) Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols. Synthesis, 130-132.
23. Thompson AS, Humphrey GR, Demarco AM, Mathre DJ, Brabowski EJJ. (1993) Direct conversion of activated alcohols to azides using diphenyl phosphorazidate. A practical alternative to Mitsunobu conditions. The Journal of Organic Chemistry, 58, 5886-5888.
24. Kitamura M, Koga T, Yano M, Okauchi T. (2012) Direct synthesis of organic azides from alcohols using 2-azido-1, 3-dimethylimidazolinium hexafluorophosphate. Synlett, 23, 1335-1338.
25. Kitamura M, Yano M, Tashiro N, Miyagawa S, Sando M, Okauchi T. (2011) Direct synthesis of organic azides from primary amines with 2-azido- 1, 3-dimethylimidazolinium hexafluorophosphate. European Journal of Organic Chemistry, 458-462.
26. Goddard-Borger ED, Stick RV. (2007) An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. Organic Letters, 9, 3797-3800.
27. Fischer N, Goddard-Borger ED, Greiner R, Klapötke TM, Skelton BW, Stiestorfer J. (2012) Sensitivities of some imidazole-1-sulfonyl azide salts. The Journal of Organic Chemistry, 77, 1760-1764.
28. Ye H, Liu R, Li D, Liu Y, Yuan H, Guo W, Zhou L, Cao X, Tian H, Shen J, Wang PG. (2013) A safe and facile route to imidazole-1-sulfonyl azide as a diazotransfer reagent. Organic Letters, 15, 18-21.
29. Guerin DJ, Horstmann TE, Miller SJ. (1999) Amine-catalyzed addition of azide ion to α, β-unsaturated carbonyl compounds. Organic Letters, 1, 1107-1109.
30. Yamashita S, Iso K, Kitajima K, Himuro M, Hirama M. (2011) Total synthesis of cortistatins A and J. The Journal of Organic Chemistry, 76, 2408-2425.
31. Kouko T, Matsumura K, Kawasaki T. (2005) Total synthesis of marine bisindole alkaloids, (+)-hamacanthins A, B and (-)-antipode of cis-dihydrohamacanthin B. Tetrahedron, 61, 2309-2318. (Pubitemid 40228792)
32. Evans EA, Britton TC. (1987) Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of α-amino acids. Journal of the American Chemical Society, 109, 6881-6883.
33. Pronin SV, Kozmin SA. (2010) Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor. Journal of the American Chemical Society, 132, 14394-14396.
34. Pronin SV, Martinez A, Kuznedelov K, Severinov K, Shuman HA, Kozmin SA. (2011) Chemical synthesis enables biochemical and antibacterial evaluation of streptolydigin antibiotics. Journal of the American Chemical Society, 133, 12172-12184.
35. Das J, Koswatta PB, Jones JD, Yousufuddin M, Lovely CJ. (2012) Total syntheses of kealiinines A-C. Organic Letters, 14, 6210-6213.
36. Koswatta PB, Lovely CJ, (2010) Concise total synthesis of naamine G and naamidine H. Chemical Communications, 46, 2148-2150.
37. Nishimura T, Unni AK, Yokoshima S, Fukuyama T. (2011) Concise total synthesis of (+)-lyconadin A. Journal of the American Chemical Society, 133, 418-419.
38. Nishimura T, Unni AK, Yokoshima S, Fukuyama T. (2013) Total syntheses of lyconadinds A-C. Journal of the American Chemical Society, 135, 3243-3247.
39. Magnus P, Lacour J. (1992) New trialkylsilyl enol ether chemistry. Direct β-azido functionalization of triisopropylsilyl enol ethers. Journal of the American Chemical Society, 114, 767-769.
40. White JD, Li Y, Kim J, Terinek M. (2013) a novel synthesis of (-)-huperzine A via tandem intramolecular aza-Prins cyclization-cyclobutane fragmentation. Organic Letters, 15, 882-885.
41. Gibble GW. (2000) Recent developments in indole synthesis-methodology and applications. Journal of the Chemical Society Perkin Transactions 1, 1045-1075.
42. Pelkey ET, Gribble GW. (1997) Synthesis of 2-nitroindoles via the Sundberg indole synthesis. Tetrahedron Letters, 38, 5603-5606. (Pubitemid 27321133)
43. Fresneda PM, Molina P, Delgado S. (1999) A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids. Tetrahedron Letters, 40, 7275.
44. Mendenhall D, Smith PAS. (1973) 2-Nitrocarbazole. Organic Synthesis Collective, 5, 829-832.
45. Okano K, Fujiwara H, Noji T, Fukuyama T, Tokuyama H. (2010) Total synthesis of dictyodendrin A and B. Angewandte Chemie International Edition, 49, 5925-5929.
46. Tokuyama H, Okano K, Fujiwara H, Noji T, Fukuyama T. (2011) Total synthesis of dictyodendrins A-E. Chemistry An Asian Journal, 6, 560-572.
47. Pudlo M, Csányi D, Moreau F, Hajós G, Riedl Z, Sapi J. (2007) First Suzuki-Miyaura type cross-coupling of orthoazidobromobenzenewith arylboronic acids and its application to the synthesis of fused aromatic indole-heterocycles. Tetrahedron, 63, 10320-10329. (Pubitemid 47334829)
48. Pumphrey AL, Dong H, Driver TG. (2012) RhII 2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides. Angewandte Chemie International Edition, 51, 5920-5923.
49. Dong H, Latka RT, Driver TG. (2011) Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin. Organic Letters, 13, 2726-2729.
50. Chiyoda K, Shimokawa J, Fukuyama T. (2012) Total syntheses of all the amathaspiramides. Angewandte Chemie International Edition, 51, 2505-2508.
51. Yamada K, Mogi Y, Mohamed MA, Takasu K, Tomioka K. (2012) Total synthesis of (+)-trans-dihydronarciclasine utilizing asymmetric conjugate addition. Organic Letters, 14, 5868-5871.
52. Chaumontet M, Piccardi R, Baudoin O. (2009) Synthesis of 3, 4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: Total synthesis of coralydine. Angewandte Chemie International Edition, 48, 179-182.
53. Parsons TB, Spencer N, Tsang CW, Grainger RS. (2013) Total synthesis of kottamide E. Chemical Communications, 49, 2296-2298.
54. Molina P, Alcántara J, López-Leonardo C. (1995) Preparation of 2-substituted pyrrolines by an intramolecular Shmidt reaction of 4-substituted 3-butenyl azides. Synlett, 363-364.
55. Boyer JH, Hamer J. (1955). The Acid-catalyzed Reaction of Alkyl Azides upon Carbonyl Compounds. Journal of the American Chemical Society, 77, 951-954.
56. Frankowski KJ, Golden JE, Zeng Y, Lei Y, Aubé J (2008) Syntheses of the Stemona alkaloids (±)-stenine, (±)-neostenine, and (±)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction. Journal of the American Chemical Society, 130, 6018-6024. (Pubitemid 351620849)
57. Chen Z-H, Tu Y-Q, Zhang S-Y, Zhang F-M. (2011) Development of the intramolecular Prins cyclization/Schmidt reaction for the construction of the azaspiro [4, 4]nonane: Application to the formal synthesis of (±)-stemonamine. Organic Letters, 13, 724-727.
58. Zhao Y-M, Gu P, Tu Y-Q, Fan C-A, Zhang Q. (2008) an efficient total synthesis of (±)-stemonamine. Organic Letters, 10, 1763-1766.
59. Ma A-J, Tu Y-Q, Peng J-B, Dou Q-Y, Hou S-H, Zhang F-M, Wang S-H. (2012) Total synthesis of (-)-FR901483. Organic Letters, 14, 3604-3607.
60. Villargordo, JM, Linden A, Heimgartner H. (1996) A novel amination reaction with diphenyl phosphorazidate: synthesis of α-amino-acid derivatives, Helvetica Chimica Alta, 79, 213-219.
61. Kapat A, Nyfeler E, Giuffredi GT, Renaud P. (2009) Intramolecular Schmidt reaction involving primary azidoalcohols under nonacidic conditions:synthesis of indolizidine (-)-167B. Journal of the American Chemical Society, 131, 17746-17747.
62. Panchaud P, Ollivier C, Renaud P, Zigmantas S. (2004) Radical carboazidation: Expedient assembly of the core structure of various alkaloid families. The Journal of Organic Chemistry, 69, 2755-2759. (Pubitemid 38469032)
63. Hayashi K, Tanimoto H, Zhang H, Morimoto T, Nishiyama Y, Kakiuchi K. (2012) Efficient synthesis of α, β-unsaturated alkylimines performed with allyl cations and azides: application to the synthesis of an ant venom alkaloid. Organic Letters, 14, 5728-5731.
64. Smith Jr RH, Wladkowski BD, Taylor JE, Thompson EJ, Pruski B, Klose JR, Andrews AW, Michejda CJ. (1993) Acid-catalyzed decomposition of 1-alkyltriazolines: A mechanistic study. The Jounarl of Organic Chemistry, 58, 2097-2103.
65. Troyer TL, Muchalski H, Hong KB, Johnston JN. (2011) Origins of selectivity in Brønsted acid-promoted diazoalkane-azomethine reactions (the aza-Darzens aziridine synthesis). Organic Letters, 13, 1790-1792.
66. Feldman KS, Antoline JF. (2012) Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine. Organic Letters, 14, 934-937.
67. Zhao Y-M, Gu. P, Tu T.-Q., Zhan H-J. Zhang QW. Fan C-A. (2010) One-pot synthesis of aminoenone via direct reaction of the chloroalkyl enone with NaN3: Rapid access to polycyclic alkaloids. The Journal of Organic Chemistry, 75, 5259-5295.
68. de Miguel I, Velado M, Herradón B, Mann E. (2012) First total synthesis of the pyrrolizidine alkaloid amphorogynine C through intramolecular azide-olefin cycloaddition. European Journal of Organic Chemistry, 4347-4353.
69. Liu P, Seo JH, Weinreb SM. (2010) Total synthesis of the polycyclic fungal metabolite (±)-communesin F. Angewandte Chemie International Edition, 49, 2000-2003.
70. Seo JH, Liu P, Weinreb SM. (2010) Evolution of a strategy for total synthesis of the marine fungal alkaloid (±)-communesin F. The Journal of Organic Chemistry, 75, 2667-2680.
71. Wang Y-F, Toh KK, Ng EPJ, Chiba S. (2011) Mn(III)-mediated formal [3+3]-annulation of vinyl azides and cyclopropanols: a divergent synthesis of azaheterocycles. Journal of the American Chemical Society, 133, 6411-6421.
72. Wang, Y-F. Chiba S. (2009) Mn(III)-Mediated reactions of cyclopropanols with vinyl azides: synthesis of pyridine and 2-azabicyclo [3.3.1]non-2- en-1-ol derivatives. Journal of the American Chemical Society, 131, 12570-12572.
73. Gololobov YG, Kasukhin LF. (1992) Recent advances in the Staudinger reaction Tetrahedron, 48, 1353-1406.
74. Wong ML, Guzei IA, Kiessling LL. (2012) An asymmetric synthesis of L-pyrrolysine. Organic Letters, 14, 1378-1381.
75. Müller T, Göhl M, Lusebrink I, Dettner K, Seifert K. (2012) Cicindeloine from Stenus cicindeloides-Isolation, structure elucidation, and total synthesis. European Journal of Organic Chemistry, 2323-2330.
76. Nakahara K, Hirano K, Maehata R, Kita Y, Fujioka H. (2011) Asymmetric total synthesis of clavolonine. Organic Letters, 13, 2015 -2017.
77. Kurosawa W, Kan T, Fukuyama T. (2003) Stereocontrolled total synthesis of (-)-ephedradine A (orantine). Journal of the American Chemical Society, 125, 8112-8113. (Pubitemid 36828569)
78. Kurosawa W, Kobayashi H, Kan T, Fukuyama T. (2004) Total synthesis of (-)-ephedradine A: an efficient construction of optically active dihydrobenzodfuran-ring via C-H insertion reaction. Tetrahedron, 60, 9615-9628. (Pubitemid 39263681)
79. Uchida K, Ogawa T, Yasuda Y, Mimura H, Fujimoto T, Fukuyama T, Wakimoto T, Asakawa T, Hamashima Y, Kan T. (2012) Stereocontrolled total synthesis of (+)-UCS1025A. Angewandte Chemie International Edition, 51, 12850-12853.
80. Rolla F. (1982) sodium borohydride reactions under phase-transfer conditions: reduction of azides to amines. The Journal of Organic Chemistry, 47, 4327-4329.
81. Maiti SN, Spevak P, Reddy AVN. (1988) Alkaline earth metal mediated reduction of azides to amines. Synthetic Communications, 18, 1201-1206.
82. Reddy GV, Rao GV, Iyengar DS. (1999) a novel, simple chemoselective and practical protocol for the reduction of azides using In/NH4Cl. Tetrahedorn Letters, 40, 3937-3938. (Pubitemid 29202271)
83. Maegawa T, Takahashi T, Yoshimura M, Suzuka H, Monguchi Y, Sajiki H. (2009) Development of molecular sieves-supported palladium catalyst and chemoselective hydrogenation of unsaturated bonds in the presence of nitro groups. Advanced Synthesis and Catalyst. 351, 2091-2095.
84. Molander GA, Röss M. (1999) Total synthesis of (-)-cylindricine C. The Journal of Organic Chemistry, 64, 5183-5187.
85. Kirk DN, Wilson MA. (1971) D-homo-steroids. Part III. The preparation of D-homoandrostane derivatives: a study of the reactions of steroidal C(17)-spiro-oxirans and their derivatives. Journal of the Chemical Society C: Organic, 414-424.
86. Kondo T, Nakai H, Goto T. (1973) Synthesis of cytosinine, the nucleoside component of antibiotic blasticidin S. Tetrahedron, 29, 1801-1806.
87. Kaufmann E, Thompson RC. (1977) Reduction of organic azides by chromium(II) in aqueous solution. Journal of the American Chemical Society, 99, 1824-1830.
88. Boyer JH, Ellzey Jr SE. (1958) Reduction of the azido group with sodium borohydride. The Journal of Organic chemistry. 23, 127-129.
89. Gustafsson T, Schou M, Almqvist F, Kihlberg J. (2004) A total synthesis of hydroxylysine in protected form and investigations of the reductive opening of p-methoxybenzylidene acetals. The Journal of Organic Chemistry, 69, 8694-8701. (Pubitemid 39603028)
90. Smith PAS, Hall JH, Kan RO. (1962) The electronic character of the azido group attached to benzene rings. Journal of the American Chemical Society, 84, 485-489.
91. Yaragorla S, Muthyala R. (2010) Formal total synthesis of (-)-balanol: a ptent PKC inhibitor. Tetrahedron Letters, 51, 467-470.
92. Nicolaou KC, Bunnage ME, Koide K. (1994) Total synthesis of balanol. Journal of the American Chemical Society, 116, 8402-8403. (Pubitemid 24315623)
93. Miyaoka H, Abe Y, Sekiya N, Mitome H, Kawashima E. (2012) Total synthesis of antimalarial diterpenoid (+)-kalihinol A. Chemical Communications, 48, 901-903.
94. Miyaoka H, Abe Y, Kawashima E. (2012) Synthesis of marine diterpene isocyanide (-)-kalihinol Y and diterpene isothiocyanate (-)-10-epikalihinol I. Chemical and Pharmaceutical Bulletin, 60, 1224-1226.
95. Back TG, Baron DL, Yan K. (1993) desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies. The Journal of Organic Chemistry, 58, 2407-2413.
96. Frost JR, Pearson CM, Snaddon TN, Booth RA, Ley SV. (2012) Convergent total syntheses of callipeltosides A, B, and C. Angewandte Chemie International Edition, 51, 9366-9371.
97. Yamaguchi J, Seiple IB, Young IS, O'Malley DP, Maue M, Baran PS. (2008) Synthesis of 1, 9-dideoxy-pre-axinellamine. Angewandte Chemie International Edition, 47, 3578-3580.
98. O'Malley DP, Yamaguchi J, Young IS, Seiple IB, Baran PS. (2008) Total synthesis of (±)-axinellamines A and B. Angewandte Chemie International Edition, 47, 3581-3583.
99. Su S, Seiple IB, Young IS, Baran PS. (2008) Total synthesis of (±)-massadine and massadine chloride. Journal of the American Chemical Society, 130, 16490-16491.
100. Seiple IB, Su S, Young IS, Lewis CA, Yamaguchi J, Baran PS. (2010) Total synthesis of palau'amine. Angewandte Chemie International Edition, 49, 1095-1098.
101. Su S, Rodriguez RA, Baran PS. (2011) Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B. Journal of the American Chemical Society, 133, 13922-13925.
102. Seiple IB, Su S, Young IS, Nakamura A, Yamaguchi J, Jørgensen L, Rodriguez RA, O'Malley DP, Gaich T, Köck, Baran PS. (2011) Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines. Journal of the American Chemical Society, 133, 14710-14726.
103. Gemal AL, Luche JL. (1981) Lanthanoids in organic synthesis. 6. Reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: Synthetic and mechanistic aspects. Journal of the American Chemical Society, 103, 5454-5459.
104. Hanessian S, Vakiti RR, Dorich S, Banerjee S, Lecomte F, DelValle JR, Zhang J, Deschênes-Simard B. (2011) Total synthesis of pactamycin. Angewandte Chemie International Edition, 50, 3497-3500.
105. Hanessian S, Vakiti RR, Dorich S, Banerjee S, Lecomte F, Deschênes-Simard B. (2012) Total synthesis of pactamycin and pactamycate: a detailed account. The Journal of Organic Chemistry, 77, 9458-9472.