메뉴 건너뛰기




Volumn 15, Issue 2, 2010, Pages 1041-1073

Synthetic applications of chiral unsaturated epoxy alcohols prepared by Sharpless asymmetric epoxidation

Author keywords

Asymmetric synthesis; Epoxide ringopening; Olefin metathesis; Ring closing metathesis; Sharpless asymmetric epoxidation

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE;

EID: 77649204480     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15021041     Document Type: Article
Times cited : (43)

References (90)
  • 1
    • 18844410382 scopus 로고
    • Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization
    • Gao, Y.; Klunder, J.M.; Hanson, R.M.; Masamune, H.; Ko, S.Y.; Sharpless, K.B. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765-5780
    • Gao, Y.1    Klunder, J.M.2    Hanson, R.M.3    Masamune, H.4    Ko, S.Y.5    Sharpless, K.B.6
  • 2
    • 0003643883 scopus 로고
    • Asymmetric synthesis. The Sharpless epoxidation
    • VCH: Weinheim, Germany
    • Schinzer, D. Asymmetric synthesis. The Sharpless epoxidation. In Organic Synthesis Highlights II; VCH: Weinheim, Germany, 1995; pp. 3-8.
    • (1995) Organic Synthesis Highlights II , pp. 3-8
    • Schinzer, D.1
  • 3
    • 0001780886 scopus 로고    scopus 로고
    • Asymmetric epoxidation of allylic alcohols: The Katsuki-Sharpless epoxidation reaction
    • Katsuki, T.; Martin, V. Asymmetric epoxidation of allylic alcohols: The Katsuki-Sharpless epoxidation reaction. Org. React. 1996, 48, 1-299.
    • (1996) Org. React. , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.2
  • 4
    • 0032580376 scopus 로고    scopus 로고
    • Recent advances in olefin metathesis and its application in organic synthesis
    • Grubbs, R.H.; Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 5
    • 0034246704 scopus 로고    scopus 로고
    • Metal-mediated synthesis of medium-sized rings
    • Yet, L. Metal-mediated synthesis of medium-sized rings. Chem. Rev. 2000, 100, 2963-3007.
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 6
    • 68949096781 scopus 로고    scopus 로고
    • Metathesis in the synthesis of aromatic compounds
    • Van Otterlo, W.A.L.; de Koning, C.B. Metathesis in the synthesis of aromatic compounds. Chem. Rev. 2009, 109, 3743-3782.
    • (2009) Chem. Rev. , vol.109 , pp. 3743-3782
    • Van Otterlo, W.A.L.1    De Koning, C.B.2
  • 7
    • 1542763298 scopus 로고
    • Ring-closing metathesis and related processes in organic synthesis
    • Grubbs, R.H.; Miller, S.J.; Fu, G.C. Ring-closing metathesis and related processes in organic synthesis. Acc. Chem. Res. 1995, 28, 446-452.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 446-452
    • Grubbs, R.H.1    Miller, S.J.2    Fu, G.C.3
  • 9
    • 0038215596 scopus 로고    scopus 로고
    • Recent developments in olefin cross-metathesis
    • Connon, S. Recent developments in olefin cross-metathesis. Angew. Chem. Int. Ed. 2003, 42, 1900.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1900
    • Connon, S.1
  • 10
    • 0034734340 scopus 로고    scopus 로고
    • Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts
    • Garber, S.B.; Kingsbury, J.S.; Gray, B.L.; Hoveyda, A.H. Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts. J. Am. Chem. Soc. 2000, 122, 8168-8179.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8168-8179
    • Garber, S.B.1    Kingsbury, J.S.2    Gray, B.L.3    Hoveyda, A.H.4
  • 12
    • 0025769559 scopus 로고
    • Controlled synthesis of enantio-, regio-, and diastereomers of amino-4-pentenediols from 1,4-pentadien-3-ol via epoxy-4-pentenols I. Erythro- 1-amino-4-pentene-2,3-diols
    • Jaeger, V.; Huemmer, W.; Stahl, U.; Gracza, T. Controlled synthesis of enantio-, regio-, and diastereomers of amino-4-pentenediols from 1,4-pentadien-3-ol via epoxy-4-pentenols I. Erythro- 1-amino-4-pentene-2,3- diols. Synthesis 1991, 769-776.
    • (1991) Synthesis , pp. 769-776
    • Jaeger, V.1    Huemmer, W.2    Stahl, U.3    Gracza, T.4
  • 13
    • 0026034824 scopus 로고
    • Asymmetric sharpless epoxidation of divinylcarbinol. erythro-D and -L-4-pentenitols by hydrolysis of regioisomeric epoxy-4-pentenols
    • Jaeger, V.; Schroeter, D.; Koppenhoefer, B. Asymmetric sharpless epoxidation of divinylcarbinol. erythro-D and -L-4-pentenitols by hydrolysis of regioisomeric epoxy-4-pentenols. Tetrahedron 1991, 47, 2195-2210.
    • (1991) Tetrahedron , vol.47 , pp. 2195-2210
    • Jaeger, V.1    Schroeter, D.2    Koppenhoefer, B.3
  • 14
    • 0025848415 scopus 로고
    • Controlled synthesis of regio-, enantio-, and diastereomers of amino-4-pentenediols from 1,4-pentadien-3-ol via epoxy-4-pentenols. II. erythro- and threo-3- amino-4-pentene-1,2-diols and erythro-2-benzylamino-4-pentene-1,3- diol
    • Jaeger, V.; Stahl, U.; Huemmer, W. Controlled synthesis of regio-, enantio-, and diastereomers of amino-4-pentenediols from 1,4-pentadien-3-ol via epoxy-4-pentenols. II. erythro- and threo-3- amino-4-pentene-1,2-diols and erythro-2-benzylamino-4-pentene-1,3-diol. Synthesis 1991, 776-782
    • (1991) Synthesis , pp. 776-782
    • Jaeger, V.1    Stahl, U.2    Huemmer, W.3
  • 15
    • 0347968952 scopus 로고
    • Epoxide migrations with alpha,beta-epoxy alcohols
    • Payne, G.B. Epoxide migrations with alpha,beta-epoxy alcohols. J. Org. Chem. 1962, 27, 3819-3822.
    • (1962) J. Org. Chem. , vol.27 , pp. 3819-3822
    • Payne, G.B.1
  • 16
    • 32144432079 scopus 로고    scopus 로고
    • Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid
    • Taber, D.F.; Zhang, Z. Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid. J. Org. Chem. 2006, 71, 926-933.
    • (2006) J. Org. Chem. , vol.71 , pp. 926-933
    • Taber, D.F.1    Zhang, Z.2
  • 17
    • 10344248926 scopus 로고    scopus 로고
    • The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D
    • Parker, K.A.; Lim, Y. The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D. J. Am. Chem. Soc. 2004, 126, 15968-15969.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15968-15969
    • Parker, K.A.1    Lim, Y.2
  • 18
    • 52449099224 scopus 로고    scopus 로고
    • De novo synthesis of (+)-isofregenedol
    • Riou, M.; Barriault, L. De novo synthesis of (+)-isofregenedol. J. Org. Chem. 2008, 73, 7436-7439.
    • (2008) J. Org. Chem. , vol.73 , pp. 7436-7439
    • Riou, M.1    Barriault, L.2
  • 19
    • 0042848832 scopus 로고    scopus 로고
    • Determination of the absolute configuration of vibsanin F by asymmetric synthesis via pi-allylpalladium complex
    • Yuasa, H.; Makado, G.; Fukuyama, Y. Determination of the absolute configuration of vibsanin F by asymmetric synthesis via pi-allylpalladium complex. Tetrahedron Lett. 2003, 44, 6235-6239.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6235-6239
    • Yuasa, H.1    Makado, G.2    Fukuyama, Y.3
  • 20
    • 0012815040 scopus 로고
    • The first practical method for asymmetric epoxidation
    • Katsuki, T.; Sharpless, K.B. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc. 1980, 102, 5974-5976.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5974-5976
    • Katsuki, T.1    Sharpless, K.B.2
  • 21
    • 0037416958 scopus 로고    scopus 로고
    • Stereoselective total synthesis of muconin
    • Takahashi, S.; Kubota, A.; Nakata, T. Stereoselective total synthesis of muconin. Tetrahedron 2003, 59, 1627-1638.
    • (2003) Tetrahedron , vol.59 , pp. 1627-1638
    • Takahashi, S.1    Kubota, A.2    Nakata, T.3
  • 22
    • 0037378384 scopus 로고    scopus 로고
    • The chemistry of epoxy alcohols
    • Pena, P.C.A.; Roberts, S.M. The chemistry of epoxy alcohols. Curr. Org. Chem. 2003, 7, 555-571.
    • (2003) Curr. Org. Chem. , vol.7 , pp. 555-571
    • Pena, P.C.A.1    Roberts, S.M.2
  • 23
    • 0000830825 scopus 로고
    • The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols
    • Hanson, R.M. The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols. Chem. Rev. 1991, 91, 437-476.
    • (1991) Chem. Rev. , vol.91 , pp. 437-476
    • Hanson, R.M.1
  • 24
    • 0002733819 scopus 로고
    • New transformations of 2,3-epoxy alcohols and related derivatives. Easy routes to homochiral substances
    • Behrens, C.H.; Sharpless, K.B. New transformations of 2,3-epoxy alcohols and related derivatives. Easy routes to homochiral substances. Aldrichim. Acta 1983, 16, 67-80.
    • (1983) Aldrichim. Acta , vol.16 , pp. 67-80
    • Behrens, C.H.1    Sharpless, K.B.2
  • 28
    • 0000442271 scopus 로고    scopus 로고
    • Triple ring closing metathesis reaction: Synthesis of adjacent cyclic ethers
    • Heck, M.; Baylon, C.; Nolan, S.P.; Mioskowski, C. Triple ring closing metathesis reaction: Synthesis of adjacent cyclic ethers. Org. Lett. 2001, 3, 1989-1991.
    • (2001) Org. Lett. , vol.3 , pp. 1989-1991
    • Heck, M.1    Baylon, C.2    Nolan, S.P.3    Mioskowski, C.4
  • 30
    • 40949145592 scopus 로고    scopus 로고
    • Stereoselective total synthesis of (+)- mueggelone, a novel inhibitor of fish development
    • Yadav, J.S.; Somaiah, R.; Ravindar, K.; Chandraiah, L. Stereoselective total synthesis of (+)- mueggelone, a novel inhibitor of fish development. Tetrahedron Lett. 2008, 49, 2848-2850.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 2848-2850
    • Yadav, J.S.1    Somaiah, R.2    Ravindar, K.3    Chandraiah, L.4
  • 31
    • 0019442289 scopus 로고
    • Total synthesis of 5S,12S-dihydroxy-6,10-E,8,14-Zeicosatetraenoic acid, a new human metabolite of arachidonic acid
    • Corey, E.J.; Marfat, A.; Laguzza, B.C. Total synthesis of 5S,12S-dihydroxy-6,10-E,8,14-Zeicosatetraenoic acid, a new human metabolite of arachidonic acid. Tetrahedron Lett. 1981, 22, 3339-3342.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3339-3342
    • Corey, E.J.1    Marfat, A.2    Laguzza, B.C.3
  • 32
    • 37049076524 scopus 로고
    • Titanocene induced regioselective deoxygenation of 2,3-epoxy alcohols: A new reaction for the synthesis of allylic alcohols
    • Yadav, J.S.; Shekharam, T.; Gadgil, V.R. Titanocene induced regioselective deoxygenation of 2,3-epoxy alcohols: A new reaction for the synthesis of allylic alcohols. J. Chem. Soc. Chem. Commun. 1990, 843-844.
    • (1990) J. Chem. Soc. Chem. Commun. , pp. 843-844
    • Yadav, J.S.1    Shekharam, T.2    Gadgil, V.R.3
  • 33
    • 0038543269 scopus 로고    scopus 로고
    • Total synthesis of (-)-aspidospermine via Diastereoselective ring-closing olefin metathesis
    • Fukuda, Y.; Shindo, M.; Shishido, K. Total synthesis of (-)-aspidospermine via Diastereoselective ring-closing olefin metathesis. Org. Lett. 2003, 5, 749-751.
    • (2003) Org. Lett. , vol.5 , pp. 749-751
    • Fukuda, Y.1    Shindo, M.2    Shishido, K.3
  • 35
    • 0030665236 scopus 로고    scopus 로고
    • An efficient catalytic asymmetric epoxidation method
    • Wang, Z.; Tu, Y.; Frohn, M.; Zhang, J.; Shi, Y. An efficient catalytic asymmetric epoxidation method. J. Am. Chem. Soc. 1997, 119, 11224-11235
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11224-11235
    • Wang, Z.1    Tu, Y.2    Frohn, M.3    Zhang, J.4    Shi, Y.5
  • 36
    • 37049090482 scopus 로고
    • Cleavage of 2,3-epoxyalkyl halides by the sonochemical zinc-copper couple
    • Sarandeses, L.A.; Mourino, A.; Luche, J.L. Cleavage of 2,3-epoxyalkyl halides by the sonochemical zinc-copper couple. J. Chem. Soc. Chem. Commun. 1991, 818-820.
    • (1991) J. Chem. Soc. Chem. Commun. , pp. 818-820
    • Sarandeses, L.A.1    Mourino, A.2    Luche, J.L.3
  • 37
    • 58149316212 scopus 로고    scopus 로고
    • Total synthesis of methyl sarcophytoate, a marine natural biscembranoid
    • Ichige, T.; Okano, Y.; Kanoh, N.; Nakata, M. Total synthesis of methyl sarcophytoate, a marine natural biscembranoid. J. Org. Chem. 2009, 74, 230-243.
    • (2009) J. Org. Chem. , vol.74 , pp. 230-243
    • Ichige, T.1    Okano, Y.2    Kanoh, N.3    Nakata, M.4
  • 38
    • 18844410382 scopus 로고
    • Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization
    • Gao, Y.; Klunder, J.M.; Hanson, R.M.; Masamune, H.; Ko, S.Y.; Sharpless, K.B. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765-5780
    • Gao, Y.1    Klunder, J.M.2    Hanson, R.M.3    Masamune, H.4    Ko, S.Y.5    Sharpless, K.B.6
  • 39
    • 70349777757 scopus 로고    scopus 로고
    • Functionalized templates for the convergent assembly of polyethers: Synthesis of the HIJK rings of gymnocin A
    • Van Dyke, A.R.; Jamison, T.F. Functionalized templates for the convergent assembly of polyethers: Synthesis of the HIJK rings of gymnocin A. Angew. Chem. Int. Ed. 2009, 48, 4430-4432.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 4430-4432
    • Van Dyke, A.R.1    Jamison, T.F.2
  • 40
    • 0001599949 scopus 로고
    • An effective, practical method for the synthesis of chiral propargyl alcohols
    • Yadav, J.S.; Deshpande, P.K.; Sharma, G.V.M. An effective, practical method for the synthesis of chiral propargyl alcohols. Tetrahedron 1990, 46, 7033-7046.
    • (1990) Tetrahedron , vol.46 , pp. 7033-7046
    • Yadav, J.S.1    Deshpande, P.K.2    Sharma, G.V.M.3
  • 41
    • 0032499015 scopus 로고    scopus 로고
    • Stereoselective total syntheses of (9S)- and (9R)-HETE
    • Yadav, J.S.; Bhanu, L.R.M.; Dutta, D. Stereoselective total syntheses of (9S)- and (9R)-HETE. Tetrahedron 1998, 54, 3929-3934.
    • (1998) Tetrahedron , vol.54 , pp. 3929-3934
    • Yadav, J.S.1    Bhanu, L.R.M.2    Dutta, D.3
  • 43
    • 9244227114 scopus 로고
    • Stereocontrolled synthesis of 2,5-linked bistetrahydrofurans via the triepoxide cascade reaction
    • Hoye, T.R.; Suhadolnik, J.C. Stereocontrolled synthesis of 2,5-linked bistetrahydrofurans via the triepoxide cascade reaction. Tetrahedron 1986, 42, 2855-2862.
    • (1986) Tetrahedron , vol.42 , pp. 2855-2862
    • Hoye, T.R.1    Suhadolnik, J.C.2
  • 45
    • 34447511618 scopus 로고    scopus 로고
    • A concise stereoselective total synthesis of (2R,2'R)-threo-(+)- methylphenidate via a ring-closing metathesis protocol
    • Krishna, P.R.; Lopinti, K. A concise stereoselective total synthesis of (2R,2'R)-threo-(+)- methylphenidate via a ring-closing metathesis protocol. Synlett 2007, 1742-1744.
    • (2007) Synlett , pp. 1742-1744
    • Krishna, P.R.1    Lopinti, K.2
  • 46
    • 3142683132 scopus 로고    scopus 로고
    • Double ring-closing metathesis reaction of nitrogen-containing tetraenes: Efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives
    • Ma, S.; Ni, B. Double ring-closing metathesis reaction of nitrogen-containing tetraenes: Efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives. Chem. Eur. J. 2004, 10, 3286-3300.
    • (2004) Chem. Eur. J. , vol.10 , pp. 3286-3300
    • Ma, S.1    Ni, B.2
  • 47
    • 23844467556 scopus 로고    scopus 로고
    • Chelation-controlled reduction: An enantioselective synthesis of (-)-tarchonanthuslactone
    • Sabitha, G.; Sudhakar, K.; Reddy, N.M.; Rajkumar, M.; Yadav, J.S. Chelation-controlled reduction: An enantioselective synthesis of (-)-tarchonanthuslactone. Tetrahedron Lett. 2005, 46, 6567-6570
    • (2005) Tetrahedron Lett. , vol.46 , pp. 6567-6570
    • Sabitha, G.1    Sudhakar, K.2    Reddy, N.M.3    Rajkumar, M.4    Yadav, J.S.5
  • 48
    • 0037073815 scopus 로고    scopus 로고
    • Chelation-controlled reduction: Stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone
    • Ghosh, A.K.; Lei, H. Chelation-controlled reduction: Stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone. J. Org. Chem. 2002, 67, 8783-8788.
    • (2002) J. Org. Chem. , vol.67 , pp. 8783-8788
    • Ghosh, A.K.1    Lei, H.2
  • 50
    • 44349144401 scopus 로고    scopus 로고
    • Synthesis of bistramide A and analogues, part 1: Stereoselective access to normethyl tetrahydropyran subunit
    • Hiebel, M.; Pelotier, B.; Lhoste, P.; Piva, O. Synthesis of bistramide A and analogues, part 1: Stereoselective access to normethyl tetrahydropyran subunit. Synlett 2008, 1202-1204.
    • (2008) Synlett , pp. 1202-1204
    • Hiebel, M.1    Pelotier, B.2    Lhoste, P.3    Piva, O.4
  • 51
    • 0028897469 scopus 로고
    • Synthesis of 2,6-dideoxy-4-S-methyl-4-thio-D-ribohexopyranose, a component of the esperamycin oligosaccharide
    • Dupradeau, F.; Prandi, J.; Beau, J. Synthesis of 2,6-dideoxy-4-S-methyl- 4-thio-D-ribohexopyranose, a component of the esperamycin oligosaccharide. Tetrahedron 1995, 51, 3205-3220.
    • (1995) Tetrahedron , vol.51 , pp. 3205-3220
    • Dupradeau, F.1    Prandi, J.2    Beau, J.3
  • 52
    • 30944464654 scopus 로고    scopus 로고
    • Amphidinolide B: Asymmetric synthesis of a C7-C20 synthon
    • Gopalarathnam, A.; Nelson, S.G. Amphidinolide, B: Asymmetric synthesis of a C7-C20 synthon. Org. Lett. 2006, 8, 7-10.
    • (2006) Org. Lett. , vol.8 , pp. 7-10
    • Gopalarathnam, A.1    Nelson, S.G.2
  • 53
    • 0037424373 scopus 로고    scopus 로고
    • An enantioselective synthesis of the core unit of the non-nucleoside reverse transcriptase inhibitor taurospongin A
    • Ghosh, A.K.; Lei, H. An enantioselective synthesis of the core unit of the non-nucleoside reverse transcriptase inhibitor taurospongin A. Tetrahedron Asymmetry 2003, 14, 629-634.
    • (2003) Tetrahedron Asymmetry , vol.14 , pp. 629-634
    • Ghosh, A.K.1    Lei, H.2
  • 54
    • 0032567320 scopus 로고    scopus 로고
    • Enantioselective total synthesis of taurospongin A
    • Lebel, H.; Jacobsen, E.N. Enantioselective total synthesis of taurospongin A. J. Org. Chem. 1998, 63, 9624-9625.
    • (1998) J. Org. Chem. , vol.63 , pp. 9624-9625
    • Lebel, H.1    Jacobsen, E.N.2
  • 55
    • 0001017526 scopus 로고
    • Total synthesis of carbohydrates. 3. Efficient enantioselective syntheses of 2,6-dideoxyhexoses
    • Roush, W.R.; Brown, R.J. Total synthesis of carbohydrates. 3. Efficient enantioselective syntheses of 2,6-dideoxyhexoses. J. Org. Chem. 1983, 48, 5093-5101.
    • (1983) J. Org. Chem. , vol.48 , pp. 5093-5101
    • Roush, W.R.1    Brown, R.J.2
  • 56
    • 0001589756 scopus 로고
    • Directed openings of 2,3-epoxy alcohols via reactions with isocyanates: Synthesis of (+)-erythro-dihydrosphingosine
    • Roush, W.R.; Adam, M.A. Directed openings of 2,3-epoxy alcohols via reactions with isocyanates: synthesis of (+)-erythro-dihydrosphingosine. J. Org. Chem. 1985, 50, 3752-3757.
    • (1985) J. Org. Chem. , vol.50 , pp. 3752-3757
    • Roush, W.R.1    Adam, M.A.2
  • 57
    • 0033643441 scopus 로고    scopus 로고
    • A Concise enantioselective entry to the synthesis of deoxy-aza-sugars
    • Martin, R.; Moyano, A.; Pericas, M.A.; Riera, A. A Concise enantioselective entry to the synthesis of deoxy-aza-sugars. Org. Lett. 2000, 2, 93-95.
    • (2000) Org. Lett. , vol.2 , pp. 93-95
    • Martin, R.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 58
    • 15444367790 scopus 로고    scopus 로고
    • General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine
    • Martin, R.; Murruzzu, C.; Pericas, M.A.; Riera, A. General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine. J. Org. Chem. 2005, 70, 2325-2328.
    • (2005) J. Org. Chem. , vol.70 , pp. 2325-2328
    • Martin, R.1    Murruzzu, C.2    Pericas, M.A.3    Riera, A.4
  • 60
    • 0033575507 scopus 로고    scopus 로고
    • Practical synthesis of optically active bicyclic oxazolidinylpiperidines, chiral building blocks for preparing 1-deoxyazasugars, from serine
    • Shirai, M.; Okamoto, S.; Sato, F. Practical synthesis of optically active bicyclic oxazolidinylpiperidines, chiral building blocks for preparing 1-deoxyazasugars, from serine. Tetrahedron Lett. 1999, 40, 5331-5332.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5331-5332
    • Shirai, M.1    Okamoto, S.2    Sato, F.3
  • 61
    • 0033531159 scopus 로고    scopus 로고
    • New entry for asymmetric deoxyazasugar synthesis: Syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin
    • Asano, K.; Hakogi, T.; Iwama, S.; Katsumura, S. New entry for asymmetric deoxyazasugar synthesis: Syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin. Chem. Commun. 1999, 41-42.
    • (1999) Chem. Commun. , pp. 41-42
    • Asano, K.1    Hakogi, T.2    Iwama, S.3    Katsumura, S.4
  • 62
    • 4544291552 scopus 로고    scopus 로고
    • Sialic acids: Synthesis and biochemical properties of reversible inhibitors of UDP-N-acetylglucosamine 2-epimerase
    • Al-Rawi, S.; Hinderlich, S.; Reutter, W.; Giannis, A. Sialic acids: Synthesis and biochemical properties of reversible inhibitors of UDP-N-acetylglucosamine 2-epimerase. Angew. Chem. Int. Ed. 2004, 43, 4366-4370.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4366-4370
    • Al-Rawi, S.1    Hinderlich, S.2    Reutter, W.3    Giannis, A.4
  • 63
    • 34447307167 scopus 로고    scopus 로고
    • Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors
    • Murruzzu, C.; Alonso, M.; Canales, A.; Jimenez-Barbero, J.; Riera, A. Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors. Carbohydr. Res. 2007, 342, 1805-1812.
    • (2007) Carbohydr. Res. , vol.342 , pp. 1805-1812
    • Murruzzu, C.1    Alonso, M.2    Canales, A.3    Jimenez-Barbero, J.4    Riera, A.5
  • 64
    • 53749103362 scopus 로고    scopus 로고
    • Asymmetric synthesis of cis-4- and trans-3-hydroxypipecolic acids
    • Alegret, C.; Ginesta, X.; Riera, A. Asymmetric synthesis of cis-4- and trans-3-hydroxypipecolic acids. Eur. J. Org. Chem. 2008, 1789-1796.
    • (2008) Eur. J. Org. Chem. , pp. 1789-1796
    • Alegret, C.1    Ginesta, X.2    Riera, A.3
  • 65
    • 14544276359 scopus 로고    scopus 로고
    • Enantioselective synthesis of erythro-β-hydroxyglutamic acid
    • Ginesta, X.; Pericas, M.A.; Riera, A. Enantioselective synthesis of erythro-β-hydroxyglutamic acid. Synth. Commun. 2005, 35, 289-297.
    • (2005) Synth. Commun. , vol.35 , pp. 289-297
    • Ginesta, X.1    Pericas, M.A.2    Riera, A.3
  • 66
    • 0001713826 scopus 로고
    • Regio- and stereoselective ring opening of epoxy alcohols with organoaluminum compounds leading to 1,2-diols
    • Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Regio- and stereoselective ring opening of epoxy alcohols with organoaluminum compounds leading to 1,2-diols. Tetrahedron Lett. 1982, 23, 3597-3600.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3597-3600
    • Suzuki, T.1    Saimoto, H.2    Tomioka, H.3    Oshima, K.4    Nozaki, H.5
  • 67
    • 0001068372 scopus 로고
    • Regioselectivity of the reactions of trialkylaluminum reagents with 2,3-epoxy alcohols: Application to the synthesis of alpha -chiral aldehydes
    • Roush, W.R.; Adam, M.A.; Peseckis, S.M. Regioselectivity of the reactions of trialkylaluminum reagents with 2,3-epoxy alcohols: Application to the synthesis of alpha -chiral aldehydes. Tetrahedron Lett. 1983, 24, 1377-1380.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1377-1380
    • Roush, W.R.1    Adam, M.A.2    Peseckis, S.M.3
  • 68
    • 0008363749 scopus 로고    scopus 로고
    • Improved synthetic route to enantiomerically pure samples of the tetrahydropyran-2-ylacetic acid core associated with the phytotoxic polyketide herboxidiene
    • Banwell, M.G.; McLeod, M.D.; Premraj, R.; Simpson, G.W. Improved synthetic route to enantiomerically pure samples of the tetrahydropyran-2- ylacetic acid core associated with the phytotoxic polyketide herboxidiene. Aust. J. Chem. 2000, 53, 659-664.
    • (2000) Aust. J. Chem. , vol.53 , pp. 659-664
    • Banwell, M.G.1    McLeod, M.D.2    Premraj, R.3    Simpson, G.W.4
  • 69
    • 0030981561 scopus 로고    scopus 로고
    • Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes
    • Balasubramaniam, R.P.; Moss, D.K.; Wyatt, J.K.; Spence, J.D.; Gee, A.; Nantz, M.H. Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes. Tetrahedron 1997, 53, 7429-7444.
    • (1997) Tetrahedron , vol.53 , pp. 7429-7444
    • Balasubramaniam, R.P.1    Moss, D.K.2    Wyatt, J.K.3    Spence, J.D.4    Gee, A.5    Nantz, M.H.6
  • 70
    • 33845378115 scopus 로고
    • Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening
    • Caron, M.; Sharpless, K.B. Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening. J. Org. Chem. 1985, 50, 1557-1560.
    • (1985) J. Org. Chem. , vol.50 , pp. 1557-1560
    • Caron, M.1    Sharpless, K.B.2
  • 71
    • 0038732511 scopus 로고    scopus 로고
    • A first theoretical study on the origin of the metalmediated regioselective opening of 2,3-epoxy alcohols
    • Infante, I.; Bonini, C.; Lelj, F.; Righi, G. A first theoretical study on the origin of the metalmediated regioselective opening of 2,3-epoxy alcohols. J. Org. Chem. 2003, 68, 3773-3780.
    • (2003) J. Org. Chem. , vol.68 , pp. 3773-3780
    • Infante, I.1    Bonini, C.2    Lelj, F.3    Righi, G.4
  • 72
    • 33751498927 scopus 로고
    • Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxide
    • Chini, M.; Crotti, P.; Macchia, F. Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxide. J. Org. Chem. 1991, 56, 5939-5942.
    • (1991) J. Org. Chem. , vol.56 , pp. 5939-5942
    • Chini, M.1    Crotti, P.2    Macchia, F.3
  • 73
    • 0035935105 scopus 로고    scopus 로고
    • Efficient phthalate-tethered ring-closing metathesis as a cross-coupling reaction
    • Sakamoto, Y.; Okazaki, M.; Miyamoto, K.; Nakata, T. Efficient phthalate-tethered ring-closing metathesis as a cross-coupling reaction. Tetrahedron Lett. 2001, 42, 7633-7636.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7633-7636
    • Sakamoto, Y.1    Okazaki, M.2    Miyamoto, K.3    Nakata, T.4
  • 74
    • 0029967302 scopus 로고    scopus 로고
    • Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycols and 3-amidofuranose glycals
    • McDonald, F.E.; Gleason, M.M. Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycols and 3-amidofuranose glycals. J. Am. Chem. Soc. 1996, 118, 6648-6659.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6648-6659
    • McDonald, F.E.1    Gleason, M.M.2
  • 75
    • 0030852174 scopus 로고    scopus 로고
    • Synthesis of pyranose glycals via tungsten and molybdenum pentacarbonyl-induced alkynol cyclizations
    • McDonald, F.E.; Zhu, H.Y.H. Synthesis of pyranose glycals via tungsten and molybdenum pentacarbonyl-induced alkynol cyclizations. Tetrahedron 1997, 53, 11061-11068.
    • (1997) Tetrahedron , vol.53 , pp. 11061-11068
    • McDonald, F.E.1    Zhu, H.Y.H.2
  • 76
    • 0027371238 scopus 로고
    • A short enantioselective synthesis of N-Boc-a-amino acids from epoxy alcohols
    • Poch, M.; Alcon, M.; Moyano, A.; Pericas, M.A.; Riera, A. A short enantioselective synthesis of N-Boc-a-amino acids from epoxy alcohols. Tetrahedron Lett. 1993, 34, 7781-7784.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7781-7784
    • Poch, M.1    Alcon, M.2    Moyano, A.3    Pericas, M.A.4    Riera, A.5
  • 77
    • 0030031990 scopus 로고    scopus 로고
    • An enantioselective, stereodivergent approach to anti- and syn-α-hydroxy-β-amino acids from anti-3-amino-1,2-diols. Synthesis of the ready for coupling Taxotere side chain
    • Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. An enantioselective, stereodivergent approach to anti- and syn-α-hydroxy-β-amino acids from anti-3-amino-1,2-diols. Synthesis of the ready for coupling Taxotere side chain. Tetrahedron Asymmetry 1996, 7, 243-262.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 243-262
    • Pasto, M.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 79
    • 0000224020 scopus 로고    scopus 로고
    • A catalytic asymmetric synthesis of N-Boc-β- methylphenylalanines
    • Pasto, M.; Moyano, A.; Pericas, M.A.; Riera, A. A catalytic asymmetric synthesis of N-Boc-β- methylphenylalanines. J. Org. Chem. 1997, 62, 8425-8431.
    • (1997) J. Org. Chem. , vol.62 , pp. 8425-8431
    • Pasto, M.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 80
    • 0034129984 scopus 로고    scopus 로고
    • Enantioselective syntheses of conformationally rigid, highly lipophilic mesityl-substituted amino acids
    • Medina, E.; Moyano, A.; Pericas, M.A.; Riera, A. Enantioselective syntheses of conformationally rigid, highly lipophilic mesityl-substituted amino acids. Helv. Chim. Acta 2000, 83, 972-988.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 972-988
    • Medina, E.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 81
    • 0035939140 scopus 로고    scopus 로고
    • A new method for the enantioselective synthesis of N-Boc-α,α- disubstituted a-amino acids
    • Martin, R.; Islas, G.; Moyano, A.; Pericas, M.A.; Riera, A. A new method for the enantioselective synthesis of N-Boc-α,α-disubstituted a-amino acids. Tetrahedron 2001, 57, 6367-6374.
    • (2001) Tetrahedron , vol.57 , pp. 6367-6374
    • Martin, R.1    Islas, G.2    Moyano, A.3    Pericas, M.A.4    Riera, A.5
  • 82
    • 0033387458 scopus 로고    scopus 로고
    • Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent
    • Alcon, M.; Moyano, A.; Pericas, M.A.; Riera, A. Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent. Tetrahedron Asymmetry 1999, 10, 4639-4651.
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 4639-4651
    • Alcon, M.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 84
    • 0037019991 scopus 로고    scopus 로고
    • Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4-dihydroxyproline
    • Martin, R.; Alcon, M.; Pericas, M.A.; Riera, A. Ring-closing metathesis of chiral allylamines. Enantioselective synthesis of (2S,3R,4S)-3,4- dihydroxyproline. J. Org. Chem. 2002, 67, 6896-6901.
    • (2002) J. Org. Chem. , vol.67 , pp. 6896-6901
    • Martin, R.1    Alcon, M.2    Pericas, M.A.3    Riera, A.4
  • 85
    • 33846821876 scopus 로고    scopus 로고
    • Enantioselective synthesis of hydroxylated pyrrolidines via sharpless epoxidation and olefin metathesis
    • Murruzzu, C.; Riera, A. Enantioselective synthesis of hydroxylated pyrrolidines via sharpless epoxidation and olefin metathesis. Tetrahedron Asymmetry 2007, 18, 149-154.
    • (2007) Tetrahedron Asymmetry , vol.18 , pp. 149-154
    • Murruzzu, C.1    Riera, A.2
  • 86
    • 0037185570 scopus 로고    scopus 로고
    • Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain
    • Ginesta, X.; Pericas, M.A.; Riera, A. Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain. Tetrahedron Lett. 2002, 43, 779-782.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 779-782
    • Ginesta, X.1    Pericas, M.A.2    Riera, A.3
  • 87
    • 55349131333 scopus 로고    scopus 로고
    • Enantioselective synthesis of indolizidine alkaloid trans-209D
    • Alegret, C.; Riera, A. Enantioselective synthesis of indolizidine alkaloid trans-209D. J. Org. Chem. 2008, 73, 8661-8664.
    • (2008) J. Org. Chem. , vol.73 , pp. 8661-8664
    • Alegret, C.1    Riera, A.2
  • 88
    • 34848814420 scopus 로고    scopus 로고
    • Enantioselective synthesis of trans-4-methylpipecolic acid
    • Alegret, C.; Santacana, F.; Riera, A. Enantioselective synthesis of trans-4-methylpipecolic acid. J. Org. Chem. 2007, 72, 7688-7692.
    • (2007) J. Org. Chem. , vol.72 , pp. 7688-7692
    • Alegret, C.1    Santacana, F.2    Riera, A.3
  • 89
    • 0141632609 scopus 로고    scopus 로고
    • New stereodivergent approach to 3-amino-2,3,6- trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epidaunosamine
    • Ginesta, X.; Pasto, M.; Pericas, M.A.; Riera, A. New stereodivergent approach to 3-amino-2,3,6- trideoxysugars. Enantioselective synthesis of daunosamine, ristosamine, acosamine, and epidaunosamine. Org. Lett. 2003, 5, 3001-3004.
    • (2003) Org. Lett. , vol.5 , pp. 3001-3004
    • Ginesta, X.1    Pasto, M.2    Pericas, M.A.3    Riera, A.4
  • 90
    • 33746646366 scopus 로고    scopus 로고
    • Stereodivergent syntheses of conduramines and aminocyclitols
    • Alegret, C.; Benet-Buchholz, J.; Riera, A. Stereodivergent syntheses of conduramines and aminocyclitols. Org. Lett. 2006, 8, 3069-3072.
    • (2006) Org. Lett. , vol.8 , pp. 3069-3072
    • Alegret, C.1    Benet-Buchholz, J.2    Riera, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.