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Volumn 21, Issue 5, 2002, Pages 411-430

Pyranoside alkene templates for the synthesis of CIS-2,5-disubstituted tetrahydrofuran subunits of the acetogenins

Author keywords

2,5 disubstituted tetrahydrofuran; Acetogenins; Iodoetherification

Indexed keywords

ACETOGENIN; GLYCOSIDE; PYRANOSIDE; TETRAHYDROFURAN DERIVATIVE; TRITYL DERIVATIVE;

EID: 0036409646     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120014903     Document Type: Article
Times cited : (3)

References (47)
  • 4
  • 5
    • 0000987717 scopus 로고
    • Synthesis of acetogenins of annonaceae: A new class of bioactive polyketides
    • Recent reviews on synthesis of THF acetogenins, and Refs. [6-8]
    • Figadère, B. Synthesis of acetogenins of annonaceae: A new class of bioactive polyketides. Acc. Chem. Res. 1995, 28, 359-365, Recent reviews on synthesis of THF acetogenins, and Refs. [6-8].
    • (1995) Acc. Chem. Res. , vol.28 , pp. 359-365
    • Figadère, B.1
  • 6
    • 0028812058 scopus 로고
    • Stereoselective synthesis of oligo-tetrahydrofurans
    • Koert, U. Stereoselective synthesis of oligo-tetrahydrofurans. Synthesis 1995, 115-132.
    • (1995) Synthesis , pp. 115-132
    • Koert, U.1
  • 7
    • 0029592717 scopus 로고
    • Annonaceous acetogenins - Synthetic approaches towards a novel class of natural products
    • Hoppe, R.; Scharf, H.-D. Annonaceous acetogenins - Synthetic approaches towards a novel class of natural products. Synthesis 1995, 1447-1464.
    • (1995) Synthesis , pp. 1447-1464
    • Hoppe, R.1    Scharf, H.-D.2
  • 9
    • 0000843364 scopus 로고
    • Synthesis of (+)-(15, 16, 19, 20, 23, 24)-hexepi-uvaricin: A bis(tetrahydrofuranyl) annonaceous acetogenin analogue
    • Representative syntheses of THF containing acetogenins, and Refs. [10-18]
    • Hoye, T.R.; Hanson, P.R.; Kovelesky, A.C.; Ocain, T.D.; Zhang, Z. Synthesis of (+)-(15, 16, 19, 20, 23, 24)-hexepi-uvaricin: A bis(tetrahydrofuranyl) annonaceous acetogenin analogue. J. Am. Chem. Soc. 1991, 113, 9369-9371, Representative syntheses of THF containing acetogenins, and Refs. [10-18].
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9369-9371
    • Hoye, T.R.1    Hanson, P.R.2    Kovelesky, A.C.3    Ocain, T.D.4    Zhang, Z.5
  • 10
    • 0029923916 scopus 로고    scopus 로고
    • Highly efficient synthesis of the potent antitumor annonaceous acetogenin (+)-parviflorin
    • Hoye, T.R.; Ye, Z. Highly efficient synthesis of the potent antitumor annonaceous acetogenin (+)-parviflorin. J. Am. Chem. Soc. 1996, 118, 1801-1802.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1801-1802
    • Hoye, T.R.1    Ye, Z.2
  • 11
    • 0027936335 scopus 로고
    • A concise convergent strategy to acetogenins. (+)-Solamin and analogues
    • Trost, B.M.; Shi, Z. A concise convergent strategy to acetogenins. (+)-Solamin and analogues. J. Am. Chem. Soc. 1994, 116, 7459-7460.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7459-7460
    • Trost, B.M.1    Shi, Z.2
  • 12
    • 0029101243 scopus 로고
    • The first total synthesis of (+)-bullatacin, a potent antitumor annonaceous acetogenin, and (+)-(15, 24)-bisepi-bullatacin
    • Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. The first total synthesis of (+)-bullatacin, a potent antitumor annonaceous acetogenin, and (+)-(15, 24)-bisepi-bullatacin. J. Org. Chem. 1995, 60, 4419-4427.
    • (1995) J. Org. Chem. , vol.60 , pp. 4419-4427
    • Naito, H.1    Kawahara, E.2    Maruta, K.3    Maeda, M.4    Sasaki, S.5
  • 13
    • 0001296345 scopus 로고
    • Combined osmium-rhenium approach to synthesis of naturally occurring polyethers
    • Sinha, S.C.; Sinha-Bagchi, A.; Keinan, E. Combined osmium-rhenium approach to synthesis of naturally occurring polyethers. J. Am. Chem. Soc. 1995, 114, 1447-1448.
    • (1995) J. Am. Chem. Soc. , vol.114 , pp. 1447-1448
    • Sinha, S.C.1    Sinha-Bagchi, A.2    Keinan, E.3
  • 14
    • 0029826078 scopus 로고    scopus 로고
    • Toward chemical libraries of annonaceous acetogenins. Total synthesis of trilobacin
    • Sinha, S.C.; Sinha, A.; Yazbak, A.; Keinan, E. Toward chemical libraries of annonaceous acetogenins. Total synthesis of trilobacin. J. Org. Chem. 1996, 61, 7640-7641.
    • (1996) J. Org. Chem. , vol.61 , pp. 7640-7641
    • Sinha, S.C.1    Sinha, A.2    Yazbak, A.3    Keinan, E.4
  • 15
  • 16
    • 0033525058 scopus 로고    scopus 로고
    • Total synthesis of the cytotoxic Threo, Trans, Erythro, Cis, Threo, annonaceous acetogenin trilobin
    • Marshall, J.A.; Jiang, H. Total synthesis of the cytotoxic Threo, Trans, Erythro, Cis, Threo, annonaceous acetogenin trilobin. J. Org. Chem. 1999, 64, 971-975.
    • (1999) J. Org. Chem. , vol.64 , pp. 971-975
    • Marshall, J.A.1    Jiang, H.2
  • 17
    • 0034084222 scopus 로고    scopus 로고
    • Total synthesis of squamocin A and squamocin D, Bi-tetrahydrofuran acetogenins from annonaceae
    • Emde, U.; Koert, U. Total synthesis of squamocin A and squamocin D, Bi-tetrahydrofuran acetogenins from annonaceae. Eur. J. Org. Chem. 2000, 65, 1889-1904.
    • (2000) Eur. J. Org. Chem. , vol.65 , pp. 1889-1904
    • Emde, U.1    Koert, U.2
  • 18
    • 0035830542 scopus 로고    scopus 로고
    • Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates
    • Hu, T.-S.; Yu, Q.; Wu, Y.-L.; Wu, Y. Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J. Org. Chem. 2001, 66, 853-861.
    • (2001) J. Org. Chem. , vol.66 , pp. 853-861
    • Hu, T.-S.1    Yu, Q.2    Wu, Y.-L.3    Wu, Y.4
  • 19
    • 0028798747 scopus 로고
    • Cis 2,5-disubstituted tetrahydrofurans from pyranosides: A novel example of remote stereocontrol by the aglycone
    • Zhang, H.; Wilson, P.; Shan, W.; Ruan, Z.; Mootoo, D.R. Cis 2,5-disubstituted tetrahydrofurans from pyranosides: A novel example of remote stereocontrol by the aglycone. Tetrahedron Lett. 1995, 36, 649-652.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 649-652
    • Zhang, H.1    Wilson, P.2    Shan, W.3    Ruan, Z.4    Mootoo, D.R.5
  • 20
    • 0029885236 scopus 로고    scopus 로고
    • Bis-pyranoside alkenes: Novel templates for the synthesis of adjacently linked tetrahydrofurans
    • Ruan, Z.; Wilson, P.; Mootoo, D.R. Bis-pyranoside alkenes: Novel templates for the synthesis of adjacently linked tetrahydrofurans. Tetrahedron Lett. 1996, 37, 3619-3622.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3619-3622
    • Ruan, Z.1    Wilson, P.2    Mootoo, D.R.3
  • 21
    • 0030972666 scopus 로고    scopus 로고
    • C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans
    • Seepersaud, M.; Mootoo, D.R. C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans. Tetrahedron 1997, 53, 5711-5724.
    • (1997) Tetrahedron , vol.53 , pp. 5711-5724
    • Seepersaud, M.1    Mootoo, D.R.2
  • 22
    • 0034680726 scopus 로고    scopus 로고
    • A modular synthesis of the bis-tetrahydrofuran core of rolliniastatin from pyranoside precursors
    • Ruan, Z.; Dabideen, D.; Blumenstein, M.; Mootoo, D.R. A modular synthesis of the bis-tetrahydrofuran core of rolliniastatin from pyranoside precursors. Tetrahedron 2000, 56, 9203-9211.
    • (2000) Tetrahedron , vol.56 , pp. 9203-9211
    • Ruan, Z.1    Dabideen, D.2    Blumenstein, M.3    Mootoo, D.R.4
  • 23
    • 0027200955 scopus 로고
    • Synthetic routes to 2,5-disubstituted tetrahydrofurans
    • Harmange, J.-C.; Figadère, B. Synthetic routes to 2,5-disubstituted tetrahydrofurans. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1711-1754
    • Harmange, J.-C.1    Figadère, B.2
  • 24
    • 0001657273 scopus 로고
    • Stereocontrolled cyclofunctionalization of double bonds through heterocyclic intermediates
    • Cardillo, G.; Orena, M. Stereocontrolled cyclofunctionalization of double bonds through heterocyclic intermediates. Tetrahedron 1990, 46, 3321-3408.
    • (1990) Tetrahedron , vol.46 , pp. 3321-3408
    • Cardillo, G.1    Orena, M.2
  • 25
    • 21344483439 scopus 로고
    • A novel strategy for the preparation of substituted tetrahydrofurans based on neighboring group participation by the ring oxygen of monosaccharides
    • Wilson, P.; Shan, W.; Mootoo, D.R. A novel strategy for the preparation of substituted tetrahydrofurans based on neighboring group participation by the ring oxygen of monosaccharides. J. Carbohydr. Chem. 1994, 13, 133-140.
    • (1994) J. Carbohydr. Chem. , vol.13 , pp. 133-140
    • Wilson, P.1    Shan, W.2    Mootoo, D.R.3
  • 26
    • 33845555768 scopus 로고
    • Stereocontrolled synthesis of cis-2,5-disubstituted tetrahydrofurans and cis- and trans-linalyl oxides
    • For mechanistic discussions on the haloetherification of 5-hydroxyalkenes, and Refs. [27-30]
    • Rychnovsky, S.D.; Bartlett, P.A. Stereocontrolled synthesis of cis-2,5-disubstituted tetrahydrofurans and cis- and trans-linalyl oxides. J. Am. Chem. Soc. 1981, 103, 3963-3964, For mechanistic discussions on the haloetherification of 5-hydroxyalkenes, and Refs. [27-30].
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3963-3964
    • Rychnovsky, S.D.1    Bartlett, P.A.2
  • 27
    • 0001275598 scopus 로고
    • Modeling chemical reactivity. 7. The effect of a change in rate-limiting step on the stereoselectivity of electrophilic addition to allylic alcohols and related chiral alkenes
    • Chamberlin, A.R.; Mulholland, R.L., Jr.; Kahn, S.D.; Hehre, W.J. Modeling chemical reactivity. 7. The effect of a change in rate-limiting step on the stereoselectivity of electrophilic addition to allylic alcohols and related chiral alkenes. J. Am. Chem. Soc. 1987, 109, 672-677.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 672-677
    • Chamberlin, A.R.1    Mulholland, R.L.2    Kahn, S.D.3    Hehre, W.J.4
  • 28
    • 33845281392 scopus 로고
    • Stereoselectivity of electrophile-promoted cyclizations of γ-hydroxyalkenes. An investigation of carbohydrate-derived and model substrates
    • Reitz, A.B.; Nortey, S.O.; Maryanoff, B.E.; Liotta, D.; Monahan, R., III. Stereoselectivity of electrophile-promoted cyclizations of γ-hydroxyalkenes. An investigation of carbohydrate-derived and model substrates. J. Org. Chem. 1987, 52, 4191-4202.
    • (1987) J. Org. Chem. , vol.52 , pp. 4191-4202
    • Reitz, A.B.1    Nortey, S.O.2    Maryanoff, B.E.3    Liotta, D.4    Monahan, R.5
  • 29
    • 0000535305 scopus 로고
    • Homoallylic chiral induction in the synthesis of 2,4-disubstituted THFs by iodoetherification. Synthetic scope and chiral induction mechanism
    • Labelle, M.; Morton, H.E.; Guindon, Y.; Springer, J.P. Homoallylic chiral induction in the synthesis of 2,4-disubstituted THFs by iodoetherification. Synthetic scope and chiral induction mechanism. J. Am. Chem. Soc. 1988, 110, 4533-4540.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4533-4540
    • Labelle, M.1    Morton, H.E.2    Guindon, Y.3    Springer, J.P.4
  • 30
    • 33845185699 scopus 로고
    • Diastereoselective synthesis of 2,3-disubstituted tetrahydrofuran synthons via the iodoetherification reaction. A transition state model based on the allylic asymmetric induction
    • Labelle, M.; Guindon, Y. Diastereoselective synthesis of 2,3-disubstituted tetrahydrofuran synthons via the iodoetherification reaction. A transition state model based on the allylic asymmetric induction. J. Am. Chem. Soc. 1989, 111, 2204-2210.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2204-2210
    • Labelle, M.1    Guindon, Y.2
  • 31
    • 37049141139 scopus 로고
    • Unsaturated carbohydrates. Part XI. Isomerization and dimerization of tri-O-acetyl-D-glucal
    • Ferrier, R.J.; Prasad, N. Unsaturated carbohydrates. Part XI. Isomerization and dimerization of tri-O-acetyl-D-glucal. J. Chem. Soc. C 1969, 581-586.
    • (1969) J. Chem. Soc. C , pp. 581-586
    • Ferrier, R.J.1    Prasad, N.2
  • 32
    • 0001244908 scopus 로고
    • Acyclic stereocontrol by heteroconjugate addition-4. Anti-diastereoselection by a β-chelation effect
    • Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Acyclic stereocontrol by heteroconjugate addition-4. Anti-diastereoselection by a β-chelation effect. Tetrahedron 1986, 42, 2863-2872.
    • (1986) Tetrahedron , vol.42 , pp. 2863-2872
    • Isobe, M.1    Ichikawa, Y.2    Funabashi, Y.3    Mio, S.4    Goto, T.5
  • 33
    • 0001432336 scopus 로고
    • The synthesis of β-D-glucopyranosyl-2-deoxy-α-D-arabino-hexopyranoside
    • Lemieux, R.U.; Morgan, A.R. The synthesis of β-D-glucopyranosyl-2-deoxy-α-D-arabino-hexopyranoside. Can. J. Chem. 1965, 43, 2190-2198.
    • (1965) Can. J. Chem. , vol.43 , pp. 2190-2198
    • Lemieux, R.U.1    Morgan, A.R.2
  • 34
    • 85020988830 scopus 로고    scopus 로고
    • note
    • f than the trans isomer.
  • 35
    • 0001567312 scopus 로고
    • Phosphorous betaines derived from cycloheptene and cyclooctene oxide. Inversion of cyclooctene oxide
    • Vedejs, E.; Snoble, K.A.J.; Fuchs, P.L. Phosphorous betaines derived from cycloheptene and cyclooctene oxide. Inversion of cyclooctene oxide. J. Org. Chem. 1973, 38, 1178-1182.
    • (1973) J. Org. Chem. , vol.38 , pp. 1178-1182
    • Vedejs, E.1    Snoble, K.A.J.2    Fuchs, P.L.3
  • 36
    • 0033597743 scopus 로고    scopus 로고
    • Extended alkenyl glycosides by ruthenium-catalyzed cross-metathesis reaction and application toward novel C-linked pseudodisaccharides
    • Roy, R.; Dominique, R.; Das, S.K. Extended alkenyl glycosides by ruthenium-catalyzed cross-metathesis reaction and application toward novel C-linked pseudodisaccharides. J. Org. Chem. 1999, 64, 5408-5412.
    • (1999) J. Org. Chem. , vol.64 , pp. 5408-5412
    • Roy, R.1    Dominique, R.2    Das, S.K.3
  • 40
    • 0029556693 scopus 로고
    • Acetal templates for the synthesis of trans 2,5-disubstituted tetrahydrofurans
    • Zhang, H.; Mootoo, D.R. Acetal templates for the synthesis of trans 2,5-disubstituted tetrahydrofurans. J. Org. Chem. 1995, 60, 8134-8135.
    • (1995) J. Org. Chem. , vol.60 , pp. 8134-8135
    • Zhang, H.1    Mootoo, D.R.2
  • 41
    • 0032549530 scopus 로고    scopus 로고
    • The asymmetric dihydroxylation-haloetherification strategy for the synthesis of tetrahydrofuran containing acetogenins
    • Zhang, H.; Seepersaud, M.; Seepersaud, S.; Mootoo, D.R. The asymmetric dihydroxylation-haloetherification strategy for the synthesis of tetrahydrofuran containing acetogenins. J. Org. Chem. 1998, 63, 2049-2052.
    • (1998) J. Org. Chem. , vol.63 , pp. 2049-2052
    • Zhang, H.1    Seepersaud, M.2    Seepersaud, S.3    Mootoo, D.R.4
  • 42
    • 0032890472 scopus 로고    scopus 로고
    • A novel desymmetrization reaction of an acetogenin precursor: A formal synthesis of trilobacin and asimicin
    • Ruan, Z.; Mootoo, D.R. A novel desymmetrization reaction of an acetogenin precursor: A formal synthesis of trilobacin and asimicin. Tetrahedron Lett. 1999, 40, 49-52.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 49-52
    • Ruan, Z.1    Mootoo, D.R.2
  • 43
    • 85020995414 scopus 로고    scopus 로고
    • note
    • Although the alternative chair conformation for β-glycosides places the anomeric substituent in a stabilizing axial orientation, it appears unlikely that this would be a favorable reactive conformation, due to the high degree of congestion between the C4 and C1 axial substituents of the pyranoside and the substituent on the cis-THF ring that is being formed.
  • 44
    • 0002365919 scopus 로고
    • Human blood groups and carbohydrate chemistry
    • Lemieux, R.U.; Koto, S.; Voisin, D. Human blood groups and carbohydrate chemistry. ACS Symp. Ser. 1979, 87, 17-62.
    • (1979) ACS Symp. Ser. , vol.87 , pp. 17-62
    • Lemieux, R.U.1    Koto, S.2    Voisin, D.3
  • 47
    • 0000196303 scopus 로고
    • Stereoelectronic effects in the ring cleavage of methyl glycopyranosides using dimethylboron bromide
    • Guindon, Y.; Anderson, P.C. Stereoelectronic effects in the ring cleavage of methyl glycopyranosides using dimethylboron bromide. Tetrahedron Lett. 1987, 28, 2485-2488.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 2485-2488
    • Guindon, Y.1    Anderson, P.C.2


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