Intramolecular haloetherification and transannular hydroxycyclization of alkenes. A synthetic methodology to obtain polycyclic ethers and amines

Current Organic Chemistry

Volumn 13, Issue 9, 2009, Pages 919-938

  Montaña, Ángel M ^a   Batalla, Consuelo ^a   Barcia, Juan A ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70349972014     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527209788452135     Document Type: Review

References (132)

1. (a) Hoffmann, H. M. R. Syntheses of seven- and five-membered rings from allyl cations. Angew. Chem., 1973, 20, 877-924.
2. (b) Noyori, R.; Hayakawa, Y. Reductive dehalogenation of polyhaloketones. Org. React., 1983, 29, 163-343.
3. (c) Mann, J. The synthetic utility of oxyallyl cations. Tetrahedron, 1986, 42, 4611-4659.
4. (d) Padwa, A.; Schoffstall, A. in Advances in Cycloaddition Chemistry; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp. 1-89.
5. (e) Hosomi, A.; Tominaga, Y. in [4+3] cycloadditions, Comprehensive Organic Synthesis; Trost, B. N.; Fleming, I, Editors, Pergamon: Oxford, 1995; Vol. 5, pp. 593-615.
6. (f) West, F. G. In Advances in Cycloaddition; Lautens, M. Ed.; JAI Press: Greenwich, CT, 1997; Vol. 4, pp. 1-40.
7. (g) Harmata, M. Intramolecular cycloaddition reactions of allylic cations. Tetrahedron, 1997, 53, 6235-6280.
8. (h) Rigby, J. H.; Pigge, F. C. [4+3] cycloaddition reactions. Org. React., 1997, 51, 351-478.
9. (i) Harmata, M. in Recent Research Developments in Organic Chemistry; Transworld Research Network: Trivandrum, 1997; Vol. 1, pp. 523-535.
10. (j) Harmata, M. in Advances in Cycloaddition; Lautens, M., Ed., JAI Press: Greenwich, CT., 1997; Vol. 4, pp. 41-86.
11. (k) Cha, J. K.; Oh, J. [4 + 3] Cycloaddition reactions of cyclic oxyallyls in natural product synthesis. Curr. Org. Chem., 1998, 2, 217-232.
12. (l) El-Wareth, A.; Sarhan, A. A. O. [4+3]Cycloaddition reactions: cycloaddition of metal oxyallyl cations generated from α,α'-di- and α,α'-poly-haloketones to 1,3-dienes and anthracenes. Curr. Org. Chem., 2001, 5, 827-844.
13. (m) Harmata, M. Exploration of fundamental and synthetic aspects of the intramolecular [4 + 3] cycloaddition reaction. Acc. Chem. Res., 2001, 34, 595-605.
14. (n) Schall, A.; Reiser, O. Tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction. Chemtracts, 2004, 17, 436-441.
15. (o) Huang, J.; Hsung, R. P. Recent advances in stereoselective [4 + 3] cycloaddition reactions. Chemtracts, 2005, 18, 207-214.
16. (p) Harmata, M. Asymmetric catalytic [4+3] cycloaddition reactions. Adv. Synth. Catal., 2006, 348, 2297-2306.
17. (a) Montaña, A. M.; Ribes, S.; Grima, P. M.; García, F.; Solans, X.; Font-Bardia, M. 2-Functionalized furans as precursors of versatile cycloheptane synthons. Tetrahedron, 1997, 53, 11669-11684.
18. (b) Montaña, A. M.; Ribes, S.; Grima, P. M.; García, F. Study of cis/trans and endo/exo diastereoselectivity in the [4+3]-cycloaddition reaction of 2-functionalized furans and dimethyloxyallyl cation: preparation of versatile cycloheptane synthons. Chem. Lett., 1997, 9, 847-848.
19. (c) Montaña, A. M.; Ribes, S.; Grima, P. M.; García, F. α-Hetero-substituted furans as dienes in [4+3] cycloadditions with 1,3-dimethyloxyallyl cation for the preparation of new versatile cycloheptane synthons: a study of the factors controlling the diastereoselectivity. Acta Chem. Scand., 1998, 52, 453-460.
20. (d) Montaña, A. M.; García, F.; Grima, P. M. New synthetic methodology to prepare polyfunctionalized heptane building blocks with four stereocenters: synthesis of the (±)-C17-C23 subunit of ionomycin. Tetrahedron Lett., 1999, 40, 1375-1378.
21. (e) Montaña, A. M.; García, F.; Grima, P. M. Synthesis of the C17-C23 subunit of Ionomycin from C1-functionalized 8-oxabicyclo[3.2.1]oct-6-en-3-one. New synthetic methodology to prepare polyfunctionalized heptane building blocks with four stereocenters. Tetrahedron, 1999, 55, 5483-5504.
22. (f) Montaña, A. M.; Fernández, D. Enantioselective synthesis of trans-fused bicyclo[5.3.0]decane systems via a tandem [4+3] cycloaddition-Nicholas Reaction. Tetrahedron Lett., 1999, 40, 6499-6502.
23. (g) Montaña, A. M.; Fernández, D.; Pagès, R.; Filippou, A. C.; Kociok-Köhn, G. Enantioselective synthetic methodology to prepare trans-fused bicyclo[5.3.0]decane systems: an approach to the synthesis of the pseudoguaiane carbon framework. Tetrahedron, 2000, 56, 425-439.
24. (h) Montaña, A. M.; Grima, P. M. New methodology for the [4+3] cycloaddition reactions: generation of oxyallyl cations from α,α '-diiodoketones under sonochemical or thermal conditions. Tetrahedron Lett., 2001, 42, 7809-7813.
25. (i) Montaña, A. M.; Grima, P. M. Induction of asymmetry on the [4+3] cycloaddition reaction of C(2)-functionalized furans. Tetrahedron Lett., 2002, 43, 2017-2021.
26. (j) Montaña, A. M.; Grima, P. M. Asymmetry induction on the [4C(4π) +3C(2π)] cycloaddition reaction of C2-functionalized furans: influence of the chiral auxiliary nature. Tetrahedron, 2002, 58, 4769-4786.
27. (k) Montaña, A. M.; Grima, P. M. Generation of oxyallyl cations by reduction of α,α '-diiodoketones under sonochemical or thermal conditions: Improved methodology for the [4C(4π)+3C(2π)] cycloaddition reactions. Synth. Commun., 2003, 32, 265-279.
28. (l) Montaña, A. M.; García, F.; Batalla, C. C1-C2 cleavage of C1-functionalized 8-oxabicyclo-[3.2.1]-oct-6-en-3-one. Stereoselective preparation of 4-substituted butenolides. Tetrahedron Lett., 2004, 45, 8549-8552.
29. (m) Montaña, A. M.; García, F.; Batalla, C. Introduction of a new stereocenter on C(1)-functionalized 8-oxabicyclo [3.2.1]oct-6-en-3-ones by a regio- and stereoselective electrophilic addition. Obtention of polyfunctionalized cycloheptanes with five stereocenters. Lett. Org. Chem., 2005, 2, 480-484.
30. (n) Montaña, A. M.; García, F.; Batalla, C. New methodology to prepare polyfunctionalized cycloheptane synthons, with four stereocenters, by hydrolytic cleavage of the oxygen bridge in C(1)-functionalized 8-oxabicyclic [4+3]-cycloadducts. Lett. Org. Chem., 2005, 2, 475-479.
31. (o) Montaña, A. M.; Barcia, J. A. New synthetic methodology for 3-aminotropones. Tetrahedron Lett., 2005, 46, 8475-8478.
32. 2. Tetrahedron Lett., 2006, 47, 8299-8304.
33. (q) Montaña, A.M.; Ponzano, S.; Kociok-Köhn, G.; Font-Bardia, M.; Solans, X. Versatile methodology to synthesize oxygen-bridged nine- and ten-membered cycloalkanes by the hypoiodite reaction. Eur. J. Org. Chem., 2007, 26, 4383-4401.
34. (r) Montaña, A. M.; Barcia, J. A.; Kociok-Köhn, G.; Font-Bardia, M.; Solans, X. Synthesis of 3-aminotropones from N-Boc-protected furan-2-amine by cycloaddition reactions and subsequent rear-rangement. Helv. Chim. Acta, 2008, 91, 187-208.
35. Hartung, I. V.; Hoffmann, H. M. R. 8-Oxabicyclo[3.2.1]oct-6-enones: Application to the asymmetric synthesis of polyoxygenated building blocks. Angew. Chem. Int. Ed., 2004, 43, 1934-1949.
36. a) Denes, F.; Beaufils, F.; Renaud, P. Preparation of five-membered rings via the translocation-cyclization of vinyl radicals. Synlett., 2008, 16, 2389-2399.
37. b) Ishibashi, H. Controlling the regiochemistry of radical cyclizations. Chem. Record, 2006, 6, 23-31.
38. c) Landais, Y. Stereocontrol in reactions of cyclic and acyclic β-silyl radicals. Compt. Rend. Chim., 2005, 8, 823-832.
39. d) Ishibashi, H.; Tamura, O. Control of regiochemistry of radical cyclizations and applications to the synthesis of physiologically active compounds. Yuki Gosei Kagaku Kyokaishi, 2004, 62, 324-334.
40. e) Lombardo, M.; Trombini, C. The reaction of nitrones with organometallic compounds: scope, limitations and synthetic applications. Curr. Org. Chem., 2002, 6, 695-713.
41. f) Hartung, J.; Gottwald, T.; Spehar, K. Selectivity in the chemistry of oxygen-centered radicals - the formation of carbon-oxygen bonds. Synthesis, 2002, 11, 1469-1498.
42. g) Tokuyama, H.; Fukuyama, T. Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products. Chem. Record., 2002, 2, 37-45.
43. h) Hartung, J. Stereoselective construction of the tetrahydrofuran nucleus by alkoxyl radical cyclizations. Eur. J. Org. Chem., 2001, 4, 619-632.
44. i) Ikeda, M. Regio- and stereo-control in radical cyclizations and applications to natural products syntheses. Yakugaku Zasshi, 1997, 117, 973-990.
45. j) Cristobal-López, J.; Fraser-Reid, B. Parlaying C-O chirality into C-C chirality: improving the cost/benefit ratio of carbohydrate templates. J. Chem. Soc. Chem. Commun., 1997, 23, 2251-2257.
46. k) Curran, D. P. Synthesis of substituted cyclooctanols by a samarium(II) iodide promoted 8-endo radical cyclization process. On the stereoselectivity of radical 4-exo-trig-cyclization of optically active ethyl (2E)-6-oxohex-2-enoates with samarium(II) iodide. Chemtracts: Org. Chem., 1994, 7, 351-354.
47. Schneiders, N.; Gottwald, T.; Hartung, J. On the stereoselectivity of alkenoxyl radical 6-exo-trig cyclizations. Eur. J. Org. Chem., 2009, 6, 797-800.
48. Haufe, G.; Kleinpeter, E. Transannular reactions of cycloalkenes, cycloalkadienes, and cycloalkatrienes. Synthesis of 9-azabicyclononanes from (Z,Z)-1,5-cyclooctadiene. Tetrahedron Lett., 1982, 23, 3555-3558.
49. a) Haufe, G.; Mühlstädt, M. Transannular reactions of cycloalkenes, cycloalkadienes, and cycloalkatrienes. Transannular O-heterocyclization of twelve- and thirteen-membered trienes by methoxybromination procedure. Tetrahedron Lett., 1984, 25, 1777-1780.
50. b) Haufe, G. Transannular reactions of cycloalkenes, cycloalkadienes, and cycloalkatrienes. Electrophile and solvent dependent syntheses of cyclic ethers from (Z,Z)-cycloocta-1,5-diene. Tetrahedron Lett., 1984, 25, 4365-4368.
51. Haufe, G; Rolle, U.; Kleinpeter, E.; Kivikoski, J.; Rissanen, K. Transannular reactions of cycloalkenes, cycloalkadienes, and cycloalkatrienes. N-Heterocyclization in electrophilic haloamidation reactions of 1,5-cyclooctadiene. Synthesis and rearrangements of the granatanine and homonortropane skeletons. J. Org. Chem., 1993, 58, 7084-7088.
52. a) Ponsold, K.; Ihn, W. Addition of cyanamide and halogen to olefins. New synthesis of vicinal halocyanamines and aziridines. Tetrahedron Lett., 1970, 1125-1128.
53. b) Jung, S. H.; Kohn, H. Stereoselective synthesis of vicinal diamines from alkenes and cyanamide. J. Am. Chem. Soc. 1985, 107, 2931-2943.
54. Suarez, E.; Francisco, C. G.; Hernández, R.; León, E. I.; Salazar, J. A. Aminoselenenylation of alkenes: syntheses of β-phenylseleno carbamates and β-phenylseleno cyanamides. J. Chem. Soc., Perkin Trans. I, 1990, 2417-2427.
55. (a) Gómez-Aranda, V.; Barluenga, J.; Asensio, G.; Yus, M. Heterocyclic synthesis by means of mercuric salts. Synthesis of bicyclic systems. Tetrahedron Lett., 1972, 13, 3621-3622.
56. b) Barluenga, J.; Pérez-Prieto, J.; Bayón, A. M.; Asensio, G. The question of the reversibility in the aminomercuration of olefins. Synthesis of N-aryl-9-azabicyclo[4.2.1]- and [3.3.1]nonanes by aminomercuration of cis-cis-1,5-cyclooctadiene. Tetrahedron, 1984, 40, 1199-1204.
57. c) Barluenga, J.; Pérez-Prieto, J.; Asensio, G.; García-Granda, S.; Salvado, M. A. A study on the aminomercuration-nucleophilic demercuration of cis,cis-1,5-cyclooctadiene. Stereoselective synthesis of 2,6-disubstituted-9-azabicyclo[3.3.1]nonanes. Tetrahedron, 1992, 48, 3813-3826.
58. d) Gómez-Aranda, V.; Barluenga, J.; Aznar, F. Addition of aromatic amines to alkenes in the presence of thallium(III) acetate. Synthesis, 1974, 504-505.
59. e) Barluenga, J.; Jiménez, C.; Nájera, C.; Yus, M. Amidomercuriation: a general addition of amides and related compounds to olefins. J. Chem. Soc., Perkin Trans. I, 1983, 591-593.
60. f) Barluenga, J.; Jiménez, C.; Nájera, C.; Yus, M. Stereoselective addition of carbamates to unsaturated systems by means of mercury(II) nitrate. Synthesis of saturated nitrogen-containing heterocycles. J. Heterocycl. Chem., 1984, 21, 1733-1736.
61. g) Barluenga, J.; Jiménez, C.; Nájera, C.; Yus, M. Sulfonamidomercuration of olefins and subsequent reductive demercuration or bromodemercuration. J. Chem. Soc., Perkin Trans. I, 1984, 721-725.
62. a) Bordwell, F. G.; Douglass, M. L. Reduction of alkylmercuric hydroxides by sodium borohydride. J. Am. Chem. Soc., 1966, 88, 993-999.
63. b) Stetter, H.; Meissner, H. J. 2,6-Dioxaadamantane. Tetrahedron Lett., 1966, 7, 4599-4602.
64. a) Cope, A. C.; Mckervey, A.; Weinshenker, N. M. Synthetic approaches to oxygen-bridged cyclooctyl compounds. J. Org. Chem., 1969, 34, 2229-2231.
65. b) Labows, J. N.; Swern, D. Pseudohalogens. Addition of pseudohalogens to 1,5-cyclooctadiene. J. Org. Chem., 1972, 37, 3004-3006.
66. a) Scarborough, R. M.; Smith III, A. B.; Barnette, W. E.; Nicolaou, K. C. Organoselenium-induced ring closures: cyclization of dienes with PhSeOH to form cyclic ethers. J. Org. Chem., 1979, 44, 1742-1744.
67. b) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. N-Phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). Two versatile carriers of the phenylseleno group. Oxyselenation of olefins and a selenium-based macrolide synthesis. J. Am. Chem. Soc., 1979, 101, 3704-3706.
68. c) Uemura, S.; Toshimitsu, A.; Aoai, T.; Okano, M. Phenylselenenyl chloride as a reagent for the facile preparation of cyclic ethers from diolefins. Tetrahedron Lett., 1980, 21, 1533-1536.
69. d) Uemura, S.; Toshimitsu, A.; Aoai, T.; Okano, M. Oxyselenation of cycloocta-1, 5-diene. Solvent-controlled formation of 9-oxabicyclo[3.3.1]- and -[4.2.1]nonane derivatives. J. Chem. Soc., Chem. Commun., 1979, 610-611.
70. e) Toshimitsu, A.; Aoai, T.; Uemura, S.; Okano, M. Oxyselenation of diolefins with phenyl selenocyanate and copper(II) chloride. Synthesis of cyclic ethers. J. Org. Chem., 1981, 46, 3021-3026.
71. f) Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. Phenylselenenyl chloride in acetonitrile-water. A highly convenient reagent for hydroxyselenation of olefins and preparation of cyclic ethers from dienes. Tetrahedron, 1985, 41, 5301-5306.
72. a) Franz, H. J.; Hobold, W.; Hohn, R.; Müller-Hagen, G.; Müller, R.; Pritzkow, W.; Schmidt, H. Homodimerization conjugated dienes with five carbon atoms. J. Prakt. Chem., 1970, 312, 622-634.
73. b) Haufe, G.; Muhlstädt, M.; Graefe, Reaction of (Z,Z)-1,5-cyclononadiene with N-bromosuccinimide in the presence of water or methanol. Transannular reactions of cycloalkadienes and cycloalkatrienes. J. Monatsh. Chem., 1977, 108, 1431-1439.
74. Kocovsky, P.; Stieborova, I. Participation of ambident neighboring groups in hypobromous acid addition to some steroidal olefins. Competition of electronic and stereoelectronic effects. J. Chem. Soc. Perkin Trans. I, 1987, 1969-1974.
75. Edelsbacher, A.; Urban, E; Weidenauer, W. Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4, 7-methanoisobenzofuranones. Monatsh. Chem., 1992, 123, 741-747.
76. Mostler, U.; Urban, E. Synthesis and determination of configuration of a potential antimicrobial 5,6-dihydroxyisobenzofuranone. Monatsh. Chem. 1989, 120, 349-355.
77. Stejskal, R.; Urban, E.; Vollenkle, H. Synthesis and determination of configuration of potential antimicrobial 5,6-dihydroxyisobenzofuranones. Monatsh. Chem., 1991, 122, 145-156.
78. Aufreiter, U.; Fuchs, M.; Urban, E. Synthesis of 5,6-dihydroxy-4,7-methanoisobenzofuranones. Arch. Pharm., 1992, 325, 579-584.
79. Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols. J. Am. Chem. Soc., 1982, 104, 4659-4665.
80. Lok, K. P.; Jakovac, I. J.; Jones, J. B. Preparations of enantiomerically pure exo- and endo-bridged bicyclic 2.2.1 and 2.2.2 chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of meso diols. J. Am. Chem. Soc., 1985, 107, 2521-2526.
81. Abdel-Nour, R.; Schneider, K.; Urban, E. Synthesis of 4,7-dihydroxyperhydroisobenzofuran-1-one and comparison with Zwergal's structure of garlicin. Liebigs Ann. Chem., 1992, 4, 383-386.
82. Urban, E.; Jaeger, W.; Koch, H. P. Model compounds for garlicin and their antimicrobial activity in the growth-test of yeast. Sci. Pharm., 1989, 57, 451-455.
83. Zwergal, A. Active principles of Allium sativum. Pharmazie, 1952, 7, 245-256
84. Buchs, P.; Ganter, C. Heterotricyclodecanes. A further approach to 2,6-dioxatricyclo[3.3.2.03,7]decane. Helv. Chim. Acta, 1980, 63, 1420-1424.
85. a) Smith, P. A. S.; Baer, D. R. The Demjanov and Tiffeneau-Demjanov ring expansions. Org. React., 1960, 11, 157-188.
86. b) Evans, D. A.; Carroll, G. L.; Truesdale, L. K. Synthetic applications of trimethylsilyl cyanide. Efficient synthesis of β-aminomethyl alcohols. J. Org. Chem., 1974, 39, 914-917.
87. (a) Bower, K. G.; Mann, J. Oxyallyls in synthesis: preparation of tricyclic thromboxane A2 analogues. Tetrahedron Lett., 1985, 26, 4411-4412.
88. (b) Bower, K. G.; Mann, J.; Walsh, E. B.; Howarth, O. W. Thromboxane A2 analogs from 8-oxabicyclo[3.2.1]oct-6-en-3-ones. J. Chem. Soc. Perkin Trans. I, 1987, 1657-1666.
89. Hoffmann, H. M. R. New synthetic methods. The cycloaddition of allyl cations on 1,3-dienes: a general method for the synthesis of seven-membered carbocycles. Angew. Chem., 1984, 96, 29-48.
90. Hamberg, M.; Svensson, J.; Samuelsson, B. Thromboxanes. New group of biologically active compounds derived from prostaglandin endoperoxides. Proc. Natl. Acad. Sci. USA, 1975, 72, 2994-2998.
91. Lautens, M.; Belter, R. K.; Lough, A. J. Silacupration of oxabicyclic compounds. An interrupted ring opening reaction. J. Org. Chem., 1992, 57, 422-424.
92. Appendino, G.; Jakupovic, J.; Cravotto, G.; Biavatti-Weber, M. The reaction of 6,8-disubstituted E,E-germacra-1(10),4-diene 4-epoxides with oxyphilic reagents. Tetrahedron, 1997, 53, 4681-4692.
93. Hancock, R. D.; Martell, A.E. Hard and soft acid-base behaviour in aqueous solution: steric effects make some metal ions hard: a quantitative scale of hardness-softness for acids and bases. J. Chem. Ed., 1996, 73, 654-656.
94. a) Renold, W.; Ohloff, G.; Norin, T. New olefinic cyclizations by oxymetalation. Conversion of (-)-elemol to (-)-selina-4α,11-diol (cryptomeridiol) and (-)-guai-1(10)-ene-4α,11-diol. Helv. Chim. Acta, 1979, 62, 985-993.
95. b) Anteunis, M.; De Smet, A. Cyclothallation of myrcene. Synthesis, 1974, 868.
96. Reinecke, J.; Hoffmann, H. M. R. First synthesis of the functionalized dioxatricyclic core structure of dictyoxetane and proposed biogenesis in Dictyota dichotoma. Chem. Eur. J., 1995, 1, 368-373.
97. a) Braddock, D. C.; Millan, D. S.; Pérez-Fuertes, Y.; Pouwer, R. H. Sheppard, R. N.; Solanki, S.; White, A. J. P. Bromonium ion induced transannular oxonium ion formation-fragmentation in model obtusallene systems and structural reassignment of obtusallenes. J. Org. Chem., 2009, 74, 1835-1841.
98. b) Ferraz, H. M. C.; Ribeiro, C. M.; Grazini, M. V. A.; Brocksom, T.J.; Brocksom, U. Cyclization of unsaturated monoterpenic alcohols mediated by thallium(III) salts. Tetrahedron Lett., 1994, 35, 1497-1500.
99. a) Wittenberg, J.; Beil, W.; Hofmann, H. M. R. Synthesis of dioxatricycle segments of dictyoxetane. Oxygenated 6,8-dimethyl-2,7-dioxatricyclo [4.2.1.03,8]nonanes show antitumor activity. Tetrahedron Lett., 1998, 39, 8259-8262.
100. b) Proemmel, S.; Wartchow, R.; Hofmann, H. M. R. Synthesis and studies of marine natural products: the dictyoxetane core from 8-oxabicyclo[3.2.1]oct-6-en-3-ones. Tetrahedron, 2002, 58, 6199-6206.
101. a) Pullaiah, K. C.; Suprapaneni, R. K.; Rao, C. B.; Albizati, K. F.; Faulkner, D. J.; Cunheng, H.; Clardy, J. Dictyoxetane, a novel diterpene from the brown alga Dictyota dichotoma from the Indian Ocean. J. Org. Chem., 1985, 50, 3665-3666.
102. b) Rao, C. B.; Pullaiah, K. C.; Suprapaneni, R. K.; Albizati, K. F.; Faulkner, D. J.; Cunheng, H.; Clardy, J. The diterpenes of Dictyota dichotoma from the Indian Ocean. J. Org. Chem., 1986, 51, 2736-2742.
103. a) Stark, C. B. W.; Eggert, U.; Hoffmann, H. M. R. Chiral allyl cations in cycloadditions to furan: synthesis of 2-(1′-phenylethoxy)-8-oxabicyclo [3.2.1]oct-6-en-3-one in high enantiomeric purity. Angew. Chem. Int. Ed. Engl., 1998, 37, 1266-1268.
104. b) Stark, C. B. W.; Pierau, S.; Wartchow, R.; Hoffmann, H. M. R. Chiral allyl cations are captured by furan with 100% stereoselectivity: synthesis of enantiopure 2-alkoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones by low-temperature [4+3] cycloaddition. Chem. Eur. J., 2000, 6, 684-691.
105. c) Beck, H.; Stark, C. B. W.; Hoffmann, H. M. R. Chiral allyl cations are captured by furan with 100% stereoselectivity: synthesis of enantiopure 2-alkoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones by low-temperature [4+3] cycloaddition. Org. Lett., 2000, 2, 883-886.
106. a) Lane, C. F. Sodium cyanoborohydride, a highly selective reducing agent for organic functional groups. Synthesis, 1975, 135-146.
107. b) Borch, R. F.; Bernstein, M. D. Durst, H. D. Cyanohydridoborate anion as a selective reducing agent. J. Am. Chem. Soc., 1971, 93, 2897-2904.
108. c) Mori, K.; Sugai, T.; Maeda, Y.; Okazaki, Y.; Noguchi, T.; Naito, H. Synthesis of the racemic and optically active forms of gizzerosine, the inducer of gizzard erosion in chicks. Tetrahedron, 1985, 41, 5307-5311.
109. d) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. studies on direct and indirect reductive amination procedures. J. Org. Chem., 1996, 61, 3849-3862.
110. Grainger, R. S.; Owoare, R. B. Selective 1,5-alkylidenecarbene insertion reactions on [3.2.1] oxabicyclic ethers: a new approach toward the AB ring system of ingenol. Org. Lett., 2004, 6, 2961-2964.
111. Wilson, S. R.; Sawicki, R. A. The synthesis of hemiloline: 3-aza-9oxabrandane. Tetrahedron Lett., 1978, 33, 2969-2972.
112. Glass, R. S.; Deardorff, D. R.; Gains, L. H. Pyrrolizidine synthesis by intramolecular cyclization of a substituted azacyclooctane-4,5oxide. Tetrahedron Lett., 1978, 33, 2965-2968.
113. a) Hill, A. E.; Greenwood, G.; Hoffmann, H. M. R. Cycloadditions and reactivity of 2-methoxyallyl halides. J. Am. Chem. Soc., 1973, 95, 1338-1340.
114. b) Noyori, R.; Makino, S.; Okita, T.; Kayakawa, Y. Carbon-carbon bond formations promoted by transition metal carbonyls. Method for the generation of a synthetic equivalent of unsubstituted oxyallyl via the bromo ketone-iron carbonyl reaction. New route to thujaplicins. J. Org. Chem., 1975, 40, 806-807.
115. Pascual, M. V.; Proemmel, S.; Beil, W.; Wartchow, R. Hofmann, H. M. R. Oxazatricyclic noradamantanes: stereocontrolled synthesis of functionalized scopolines, related cage molecules, and drug leads. Org. Lett., 2004, 6, 4155-4158.
116. Baxter, E. W.; Reitz, A. B. Reductive aminations of carbonyl compounds with borohydride and borane reducing agents. Org. React., 2002, 59, 1-714.
117. Montaña, A. M.; Barcia, J. A. Preparation of new antiviral agents. Spanish Patent Office, ES-P-2005-02221, 2005.
118. a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: direct assembly of 3-iodoindole cores. Angew. Chem. Int. Ed. Eng., 2003, 42, 2406-2409.
119. b) Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: A versatile trigger for assembling oxygen heterocycles. J. Am. Chem. Soc., 2003, 125, 9028-9029.
120. c) Barluenga, J.; González-Bobes, F.; Ananthoju, S. R.; GarcíaMartín, S. M.; González, J. M. Oxidative opening of cycloalkanols: An efficient entry to ω -iodo carbonyl compounds. Angew. Chem. Int. Ed. Eng., 2001, 40, 3389-3392.
121. d) Barluenga, J. Transferring iodine: more than a simple functional group exchange in organic synthesis. Pure Appl. Chem. 1999, 71, 431-436.
122. a) Green, A. E.; Luche, M. J.; Depres, J. P. Iterative three-carbon annelation. A stereoselective total synthesis of (±)-hirsutic acid C. J. Am. Chem. Soc., 1983, 105, 2435-2439.
123. b) Jia, Y.; Li, X.; Wang, P.; Wu, B.; Zhao, X.; Tu, Y. Convergent synthesis of the spiroketal core of the HIV-1 protease inhibitors the didemnaketals. J. Chem. Soc., Perkin Trans. I, 2002, 4, 565-570.
124. a) Proemmel, S.; Wartchow, R.; Hoffman, H. M. R. Synthesis and studies of marine natural products: the dictyoxetane core from 8oxabicyclo[3.2.1]oct- 6-en-3-ones. Tetrahedron, 2002, 58, 6199-6206.
125. b) Majetich, S.; Hicks, R. Carbodiimide-promoted epoxidation of olefins with dilute aqueous hydrogen peroxide. Synlett, 1996, 7, 649-651.
126. a) Adam, W.; Curci, R.; Edgard, J. O. Dioxiranes: a new class of powerful oxidants. Acc. Chem. Res., 1989, 22, 205-211.
127. b) Lusinchi, X.; Hanquet, G. Oxygen transfer reactions from an oxaziridinium tetrafluoroborate salt to olefins. Tetrahedron, 1997, 53, 13727-13738.
128. (c) Murray, R. W. Chemistry of dioxiranes. Chem. Rev., 1989, 89, 1187-1201.
129. Fringuelli, F.; Piernatti, O.; Pizzo, F.; Vaccaro, L. Ring opening of epoxides with sodium azide in water. A regioselective pHcontrolled reaction. J. Org. Chem., 1999, 64, 6094-6096.
130. a) Krishnamurthy, S.; Schubert, R. M.; Brown, H. C. Lithium triethylborohydride. Exceptionally powerful nucleophile in displacement reactions with organic halides. J. Am. Chem. Soc., 1973, 95, 1669-1671.
131. b) Gassman, P. G.; Marshall, J. L. Carbonyl neighboring group participation via enolization. J. Am. Chem. Soc., 1966, 88, 2599-2601.
132. Calculated by the ACD-Labs Software V. 8.14 of Solaris (Copyright 1994-2006 ACD-Labs).