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Volumn 18, Issue 4, 2006, Pages 223-226

A new approach for the asymmetric total synthesis of umbelactone

Author keywords

3 methyl 2 buten 1 ol; Total synthesis; Umbelactone

Indexed keywords

BUTENOLIDE; UMBELACTONE; UNCLASSIFIED DRUG;

EID: 33646255421     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20213     Document Type: Article
Times cited : (7)

References (28)
  • 1
    • 0033569863 scopus 로고    scopus 로고
    • Fissohamione, a novel furanone from Fissistigma oldhamii
    • For some recent examples, see: (a) Chia YC, Chang F, Wu Y. Fissohamione, a novel furanone from Fissistigma oldhamii. Tetrahedron Lett 1999;40:7513-7514.
    • (1999) Tetrahedron Lett , vol.40 , pp. 7513-7514
    • Chia, Y.C.1    Chang, F.2    Wu, Y.3
  • 2
    • 0033576417 scopus 로고    scopus 로고
    • Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure
    • (b) Takahashi S, Maeda K, Hirota S, Nakata T. Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure. Org Lett 1999;1:2025-2058.
    • (1999) Org Lett , vol.1 , pp. 2025-2058
    • Takahashi, S.1    Maeda, K.2    Hirota, S.3    Nakata, T.4
  • 5
    • 0031852509 scopus 로고    scopus 로고
    • A novel dimeric butenolide, glochidiolide, from the leaves of Glochidion acuminatum MUELL
    • (e) Otsuka H, Kotani K, Bando M, Kido M, Takeda Y. A novel dimeric butenolide, glochidiolide, from the leaves of Glochidion acuminatum MUELL. Chem Pharm Bull 1998;46:1180-1181.
    • (1998) Chem Pharm Bull , vol.46 , pp. 1180-1181
    • Otsuka, H.1    Kotani, K.2    Bando, M.3    Kido, M.4    Takeda, Y.5
  • 7
    • 0008051337 scopus 로고    scopus 로고
    • Chem Abstr 1996;124: 55954y.
    • (1996) Chem Abstr , vol.124
  • 8
    • 33646270657 scopus 로고    scopus 로고
    • 2(5H)-Furanones substituded in the 5 and/or in the 4 position, as anti-inflammtory agents. PCT Int. Appl. WO 91 16, 055, 1991
    • (b) Lee Gary CM, Garst ME. 2(5H)-Furanones substituded in the 5 and/or in the 4 position, as anti-inflammtory agents. PCT Int. Appl. WO 91 16, 055, 1991;
    • Lee Gary, C.M.1    Garst, M.E.2
  • 9
    • 4243385031 scopus 로고
    • Chem Abstr 1992;116:59197m.
    • (1992) Chem Abstr , vol.116
  • 10
    • 33646262918 scopus 로고    scopus 로고
    • Manufacture of gamma-crotonolactone by carbonylation of glycidol. U.S. Patent 4,968,817, 1990
    • (c) Brima TS. Manufacture of gamma-crotonolactone by carbonylation of glycidol. U.S. Patent 4,968,817, 1990;
    • Brima, T.S.1
  • 12
    • 0001613006 scopus 로고    scopus 로고
    • Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of gamma- and delta-lactones
    • (a) Yoneda E, Kaneko T, Zhang S, Onitsuka K, Takahashi S. Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of gamma- and delta-lactones. Org Lett 2000;2:441-443.
    • (2000) Org Lett , vol.2 , pp. 441-443
    • Yoneda, E.1    Kaneko, T.2    Zhang, S.3    Onitsuka, K.4    Takahashi, S.5
  • 13
    • 0001310814 scopus 로고    scopus 로고
    • Palladium-catalyzed cyclocarbonylation of terminal and internal alkynols to 2(5H)-furanones
    • (b) Yu WY, Alper H. Palladium-catalyzed cyclocarbonylation of terminal and internal alkynols to 2(5H)-furanones. J Org Chem 1997;62:5684-5687.
    • (1997) J Org Chem , vol.62 , pp. 5684-5687
    • Yu, W.Y.1    Alper, H.2
  • 14
    • 0001307443 scopus 로고    scopus 로고
    • The first examples of the palladium-catalyzed thiocarbonylation of propargylic alcohols with thiols and carbon monoxide
    • and references cited therein
    • (c) Xiao WJ, Alper H. The first examples of the palladium-catalyzed thiocarbonylation of propargylic alcohols with thiols and carbon monoxide. J Org Chem 1997;62:3422-3423 and references cited therein.
    • (1997) J Org Chem , vol.62 , pp. 3422-3423
    • Xiao, W.J.1    Alper, H.2
  • 15
    • 0008016598 scopus 로고
    • Umbelactone (4-hydroxymethyl-3-methyl-but-2-ene-4,l-olide) new constituent of Memycelon umbelatum
    • Agarwal SK, Rastogi RP. Umbelactone (4-hydroxymethyl-3-methyl-but-2-ene- 4,l-olide) new constituent of Memycelon umbelatum. Phytochemistry 1978;17:1663-1664.
    • (1978) Phytochemistry , vol.17 , pp. 1663-1664
    • Agarwal, S.K.1    Rastogi, R.P.2
  • 17
    • 0001137671 scopus 로고
    • Synthesis of the enantiomers of umbelactone: Configurational assignment of the natural product
    • (b) Ortuno RM, Bigorra J, Front J. Synthesis of the enantiomers of umbelactone: configurational assignment of the natural product. Tetrahedron 1987;43:2199-2202.
    • (1987) Tetrahedron , vol.43 , pp. 2199-2202
    • Ortuno, R.M.1    Bigorra, J.2    Front, J.3
  • 18
    • 0002317604 scopus 로고
    • (S)-β,ωDihydroxyalkyl phenyl sulfones. Synthesis by bakers' yeast reduction and use as precursors of optically active lactones
    • (c) Sato T, Okumura Y, Itai J, Fujisawa T. (S)-β, ωDihydroxyalkyl phenyl sulfones. Synthesis by bakers' yeast reduction and use as precursors of optically active lactones. Chem Lett 1988;1537-1539.
    • (1988) Chem Lett , pp. 1537-1539
    • Sato, T.1    Okumura, Y.2    Itai, J.3    Fujisawa, T.4
  • 19
    • 0029937055 scopus 로고    scopus 로고
    • An expedient synthesis of (R)-(+)-umbelactone
    • (d) Gibson CL, Handa S. An expedient synthesis of (R)-(+)-umbelactone. Tetrahedron: Asymmetry 1996;7:1281-1284.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1281-1284
    • Gibson, C.L.1    Handa, S.2
  • 20
    • 0032491544 scopus 로고    scopus 로고
    • Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: First total synthesis of (-)-4-O-(6′-hydroxy-7′(9′)- dehydro-6′,7′-dihydrogeranyl)coniferol
    • Liu ZS, Lan J, Li YL. Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (-)-4-O-(6′-hydroxy- 7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol. Tetrahedron: Asymmetry 1998;9:3755-3762.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3755-3762
    • Liu, Z.S.1    Lan, J.2    Li, Y.L.3
  • 21
    • 0030771019 scopus 로고    scopus 로고
    • Olefin metathesis in organic chemistry
    • Reviews: (a) Blechert S. Olefin metathesis in organic chemistry. Angew Chem Int Ed Engl 1997:36:2037-2056.
    • (1997) Angew Chem Int Ed Engl , vol.36 , pp. 2037-2056
    • Blechert, S.1
  • 22
    • 28244440935 scopus 로고    scopus 로고
    • Ring closing diene metathesis in organic synthesis
    • (b) Armstorng SK. Ring closing diene metathesis in organic synthesis. J Chem Soc Perkin Trans 1 1998;2:371.
    • (1998) J Chem Soc Perkin Trans 1 , vol.2 , pp. 371
    • Armstorng, S.K.1
  • 23
    • 0032580376 scopus 로고    scopus 로고
    • Recent advances in olefin metathesis and its application in organic synthesis
    • (c) Grubbs RJ, 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.J.1    Chang, S.2
  • 25
    • 0000143449 scopus 로고
    • Photooxygenation of 1-vinylcycloalkenes. The competition between ene reaction and cycloaddition of singlet oxygen
    • Herz W, Juo RR. Photooxygenation of 1-vinylcycloalkenes. The competition between ene reaction and cycloaddition of singlet oxygen. J Org Chem 1985;50:618-627.
    • (1985) J Org Chem , vol.50 , pp. 618-627
    • Herz, W.1    Juo, R.R.2
  • 27
    • 0038163433 scopus 로고    scopus 로고
    • Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond for mations
    • (b) Furstner A, Langemann K Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond for mations. J Am Chem Soc 1997;119:9130-9136.
    • (1997) J Am Chem Soc , vol.119 , pp. 9130-9136
    • Furstner, A.1    Langemann, K.2
  • 28
    • 0033533447 scopus 로고    scopus 로고
    • A stereoselective synthesis of (-)-tetrahydrolipstatin
    • (c) Ghosh AK, Liu C. A stereoselective synthesis of (-)- tetrahydrolipstatin. Chem Commun 1999;17:1743-1744.
    • (1999) Chem Commun , vol.17 , pp. 1743-1744
    • Ghosh, A.K.1    Liu, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.