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Volumn 15, Issue 2, 2003, Pages 148-155

Stereocontrolled synthesis of 1-acetylen-2,3-di-O-benzyl-tetrahydrofurans, 1,4-anhydro-arabinitol, and α,β-dihydroxy-γ-alkyl-butyrolactones

Author keywords

, dihydroxy alkylbutyrolactones; 1,4 anhydro arabinitol; 1 alkyl 2, 3 dihydroxy tetrahydrofurans; Nicholas reaction; Stereoselective synthesis

Indexed keywords

1 ACETYLEN 2,3 DI O BENZYLTETRAHYDROFURAN; 1,4 ANHYDROARABINITOL; BUTYROLACTONE; FURAN DERIVATIVE; LACTONE DERIVATIVE; RUTHENIUM DERIVATIVE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037255674     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10178     Document Type: Article
Times cited : (9)

References (32)
  • 1
    • 0012977882 scopus 로고    scopus 로고
    • New York: Chapman & Hall
    • Dictionary of natural products. New York: Chapman & Hall; vol 11 (Fourth Supplement); 1998.
    • (1998) Dictionary of Natural Products , vol.11 , Issue.FOURTH SUPPL.
  • 2
    • 0032755129 scopus 로고    scopus 로고
    • Asymmetric synthesis of tetrasubstituted tetrahydrofuran, 2-epigoniothalesdiol, employing stereoselective hydrogenation
    • (a) Yoda H, Shimojo T, Takabe K. Asymmetric synthesis of tetrasubstituted tetrahydrofuran, 2-epigoniothalesdiol, employing stereoselective hydrogenation. Synlett 1999;12:1969-1971.
    • (1999) Synlett , vol.12 , pp. 1969-1971
    • Yoda, H.1    Shimojo, T.2    Takabe, K.3
  • 3
    • 0029976480 scopus 로고    scopus 로고
    • A new efficient way to α,ω-diaminoitols by direct azidation of unprotected itols
    • (b) Glaçon V, Meslouti A, Uzan R, Demailly G, Beaupère D. A new efficient way to α,ω-diaminoitols by direct azidation of unprotected itols. Tetrahedron Lett 1996;37:3683-3686.
    • (1996) Tetrahedron Lett , vol.37 , pp. 3683-3686
    • Glaçon, V.1    Meslouti, A.2    Uzan, R.3    Demailly, G.4    Beaupère, D.5
  • 4
    • 0029955297 scopus 로고    scopus 로고
    • A new lignan from Phyllanthus virgatus
    • and references therein
    • Huang, Y-L, Chen C-C, Hsu F-L, Chen C-F. A new lignan from Phyllanthus virgatus. J Nat Prod 1996;59:520-521, and references therein.
    • (1996) J Nat Prod , vol.59 , pp. 520-521
    • Huang, Y.-L.1    Chen, C.-C.2    Hsu, F.-L.3    Chen, C.-F.4
  • 5
    • 0033580952 scopus 로고    scopus 로고
    • First total synthesis of tetrasubstituted tetrahydrofuran lignan, (-)Virgutasin
    • For a total synthesis of virgatusin, see: Yoda H, Mizutani M, Takabe K. First total synthesis of tetrasubstituted tetrahydrofuran lignan, (-)Virgutasin. Tetrahedron Lett 1999;40:4701-4702.
    • (1999) Tetrahedron Lett , vol.40 , pp. 4701-4702
    • Yoda, H.1    Mizutani, M.2    Takabe, K.3
  • 6
    • 0032536064 scopus 로고    scopus 로고
    • Synthesis of 2-C-(4-aminocarbonyl-2-thiazoyl)-1,4-anhydro-L-xylitols and their fluoro derivatives
    • Zhang HY, Yu HW, Ma LT, Min JM, Zhang LH. Synthesis of 2-C-(4-aminocarbonyl-2-thiazoyl)-1,4-anhydro-L-xylitols and their fluoro derivatives. Tetrahedron: Asymmetry 1998;9:141-149.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 141-149
    • Zhang, H.Y.1    Yu, H.W.2    Ma, L.T.3    Min, J.M.4    Zhang, L.H.5
  • 7
    • 0027942958 scopus 로고
    • A simple conversion of polyols into anhydroalditols
    • Duclos A, Fayet C, Gelas J. A simple conversion of polyols into anhydroalditols. Synthesis 1994;1087-1090.
    • (1994) Synthesis , pp. 1087-1090
    • Duclos, A.1    Fayet, C.2    Gelas, J.3
  • 8
    • 0025998871 scopus 로고
    • A novel stereoselective synthesis of (+)-Cerulenin and (+)-Tetrahydrocerulenin
    • Yoda H, Katagiri T, Takabe K. A novel stereoselective synthesis of (+)-Cerulenin and (+)-Tetrahydrocerulenin. Tetrahedron Lett 1991;32:6771-6774.
    • (1991) Tetrahedron Lett , vol.32 , pp. 6771-6774
    • Yoda, H.1    Katagiri, T.2    Takabe, K.3
  • 10
    • 37049069912 scopus 로고
    • Stereospecific synthesis of the 2,3-trans-3,4-cis trisubstituted tetrahydrofuran lignan (±)-Dihydrosesamin
    • (a) Stevens DR, Whiting DA. Stereospecific synthesis of the 2,3-trans-3,4-cis trisubstituted tetrahydrofuran lignan (±)-Dihydrosesamin. J Chem Soc, Perkin Trans 1992;1:633-637.
    • (1992) J Chem Soc, Perkin Trans , vol.1 , pp. 633-637
    • Stevens, D.R.1    Whiting, D.A.2
  • 11
    • 37049072557 scopus 로고
    • Simple synthesis of furanoid and dioxabicyclo [3.3.0]octane lignans
    • (b) Mitra J, Mitra AK. Simple synthesis of furanoid and dioxabicyclo [3.3.0]octane lignans. J Chem Soc, Perkin Trans 1992;1:1285-1286.
    • (1992) J Chem Soc, Perkin Trans , vol.1 , pp. 1285-1286
    • Mitra, J.1    Mitra, A.K.2
  • 13
    • 0342514704 scopus 로고    scopus 로고
    • 6-α,γ-acetylenic diols under Nicholas reaction conditions
    • 6-α,γ-acetylenic diols under Nicholas reaction conditions. Tetrahedron Lett 2000;41:743-746.
    • (2000) Tetrahedron Lett , vol.41 , pp. 743-746
    • Díaz, D.1    Martin, V.S.2
  • 14
    • 0001593823 scopus 로고    scopus 로고
    • Enantiocontrolled synthesis of trialkyl-substituted stereogenic carbons. A general route to cis-3,5-dialkyl γ-lactones
    • and references therein
    • (b) Diaz D, Martin VS. Enantiocontrolled synthesis of trialkyl-substituted stereogenic carbons. A general route to cis-3,5-dialkyl γ-lactones. Org Lett 2000;2:335-337, and references therein.
    • (2000) Org Lett , vol.2 , pp. 335-337
    • Diaz, D.1    Martin, V.S.2
  • 16
    • 0001651540 scopus 로고    scopus 로고
    • Double cationic propargylation: From linear to polycyclic ethers
    • We chose this cycle size because it was demonstrated in previous studies to be a good candidate to be formed by an intramolecular Nicholas reaction. See: Diaz D, Martin T, Martin VS. Double cationic propargylation: from linear to polycyclic ethers. Org Lett 2001;3:3289-3291.
    • (2001) Org Lett , vol.3 , pp. 3289-3291
    • Diaz, D.1    Martin, T.2    Martin, V.S.3
  • 17
    • 37049109459 scopus 로고
    • Regioselective reductive ring-opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protecting-group strategy. Part 1
    • Johansson R, Samuelsson B. Regioselective reductive ring-opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protecting-group strategy. Part 1. J Chem Soc, Perkin Trans 1984;1:2371-2374.
    • (1984) J Chem Soc, Perkin Trans , vol.1 , pp. 2371-2374
    • Johansson, R.1    Samuelsson, B.2
  • 18
    • 12644312578 scopus 로고
    • Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "antivated" by oxalyl chloride
    • Mancuso AJ, Huang S-L, Swern D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "antivated" by oxalyl chloride. J Org Chem 1978;43:2480-2482.
    • (1978) J Org Chem , vol.43 , pp. 2480-2482
    • Mancuso, A.J.1    Huang, S.-L.2    Swern, D.3
  • 19
    • 0000044974 scopus 로고    scopus 로고
    • Total syntheses of (+)-secosyrins 1 and 2 and (+)-syributins 1 and 2
    • For the synthesis of spiro-tetrahydrofuran derivatives using an intramolecular Nicholas cyclization, see: Mukai C, Moharram, SM, Azukizawa S, Hanaoka M. Total syntheses of (+)-secosyrins 1 and 2 and (+)-syributins 1 and 2. J Org Chem 1997;62:8095-8103.
    • (1997) J Org Chem , vol.62 , pp. 8095-8103
    • Mukai, C.1    Moharram, S.M.2    Azukizawa, S.3    Hanaoka, M.4
  • 20
    • 84982508226 scopus 로고
    • Veretherungen von diolen, triolen und hydroxycarbonsäure-derivaten über thallium(I)-alkoholate
    • Kalinowski H-O, Crass G, Seebach D. Veretherungen von diolen, triolen und hydroxycarbonsäure-derivaten über thallium(I)-alkoholate. Chem Ber 1981;114:477-487.
    • (1981) Chem Ber , vol.114 , pp. 477-487
    • Kalinowski, H.-O.1    Crass, G.2    Seebach, D.3
  • 21
    • 0012933614 scopus 로고    scopus 로고
    • note
    • The intramolecular formation of a five-membered hemiacetal favored the monooxidation of this system, even using an excess of oxidant.
  • 22
    • 0013017815 scopus 로고    scopus 로고
    • note
    • In some cases a tiny amount of the diastereoisomer was obtained but the obtained ratio was always superior to 20:1.
  • 23
    • 0033515723 scopus 로고    scopus 로고
    • An access to homopropargylic keytones from propargylic alcohols
    • Ref. 11b
    • In any case, collateral reactions such as the formation of homopropargylic ketones or products derived from hydride transfer were observed. See: (a) Soler M, Martin VS. An access to homopropargylic keytones from propargylic alcohols. Tetrahedron Lett 1999;40:2815-2816. (b) Ref. 11b.
    • (1999) Tetrahedron Lett , vol.40 , pp. 2815-2816
    • Soler, M.1    Martin, V.S.2
  • 24
    • 0026590369 scopus 로고
    • Chemoenzymatic approach to carbohydrate-derived analogoues of platelet-activating factor
    • Nicotra F, Paunch L, Russo G, Zucchelli L. Chemoenzymatic approach to carbohydrate-derived analogoues of platelet-activating factor. J Org Chem 1992;57:2154-2158.
    • (1992) J Org Chem , vol.57 , pp. 2154-2158
    • Nicotra, F.1    Paunch, L.2    Russo, G.3    Zucchelli, L.4
  • 26
    • 0001834924 scopus 로고
    • MMX, an enhanced version of MM2
    • Liotta D, editor. Greenwich, Connecticut; London, England; Jai Press Inc
    • MMX, an enhanced version of MM2: Gajewki JJ, Gilbert KE, McKelvey J. In: Advances in molecular modeling, vol. 2. Liotta D, editor. Greenwich, Connecticut; London, England; Jai Press Inc. 1990.
    • (1990) Advances in Molecular Modeling , vol.2
    • Gajewki, J.J.1    Gilbert, K.E.2    McKelvey, J.3
  • 27
    • 0012926298 scopus 로고    scopus 로고
    • PcSpartan Pro 1.0.6, Wavefunction, Inc., 2001. http://www.wavefun. com.
    • (2001) PcSpartan Pro 1.0.6
  • 28
    • 0033578597 scopus 로고    scopus 로고
    • Hydrosilylation of acetylenes with catalityc biscobalthexacarbonyl complex and its application to heteroconjugate addition methodology
    • Isobe M, Nishizawa R, Nishikawa T, Yoza K. Hydrosilylation of acetylenes with catalityc biscobalthexacarbonyl complex and its application to heteroconjugate addition methodology. Tetrahedron Lett 1999;40:6927-6932.
    • (1999) Tetrahedron Lett , vol.40 , pp. 6927-6932
    • Isobe, M.1    Nishizawa, R.2    Nishikawa, T.3    Yoza, K.4
  • 29
    • 0000117587 scopus 로고
    • An efficient synthesis of anhydroalditols and allyl C-glycosides
    • Bennek JA, Gray GR. An efficient synthesis of anhydroalditols and allyl C-glycosides. J Org Chem 1987;52:892-897.
    • (1987) J Org Chem , vol.52 , pp. 892-897
    • Bennek, J.A.1    Gray, G.R.2
  • 30
    • 33748638545 scopus 로고
    • Efficient of phenyl groups to carboxylic acids with ruthenium tetraoxide. A simple synthesis of (R)-γ-Caprolactone, the pheromone of Trogoderma granarium
    • Nuñez MT, Martin VS. Efficient of phenyl groups to carboxylic acids with ruthenium tetraoxide. A simple synthesis of (R)-γ-Caprolactone, the pheromone of Trogoderma granarium. J Org Chem 1990;55:1928-1932.
    • (1990) J Org Chem , vol.55 , pp. 1928-1932
    • Nuñez, M.T.1    Martin, V.S.2
  • 32
    • 84889582115 scopus 로고    scopus 로고
    • NMR chemicals shifts of common laboratory solvents as trace impurities
    • Gottlieb HE, Kotlyar V, Nudelman A. NMR chemicals shifts of common laboratory solvents as trace impurities. J Org Chem 1997;62:7512-7515.
    • (1997) J Org Chem , vol.62 , pp. 7512-7515
    • Gottlieb, H.E.1    Kotlyar, V.2    Nudelman, A.3


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