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Volumn 67, Issue 4, 2003, Pages 838-846

Synthesis of (+)-Aptosimon, a 4-Oxofurofuran Lignan, by erythro Selective Aldol Condensation and Stereoconvergent Cyclization as the Key Reactions

Author keywords

Aldol condensation; Aptosimon; Furofuran lignan; Lignan

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; APTOSIMON; BIOLOGICAL FACTOR; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; LIGNAN;

EID: 0041819556     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.67.838     Document Type: Article
Times cited : (14)

References (14)
  • 1
    • 0001549417 scopus 로고
    • Vier neue lignane aus Aptosimum spinescens (Thunbg.)
    • Brieskorn, C. H., and Huber, H., Vier neue lignane aus Aptosimum spinescens (Thunbg.). Tetrahedron Lett., 2221-2224 (1976).
    • (1976) Tetrahedron Lett. , pp. 2221-2224
    • Brieskorn, C.H.1    Huber, H.2
  • 2
    • 0022447035 scopus 로고
    • Synthetic methods for (Exo, exo)-and (exo-, endo)-2,6-diaryl-bicyclo[3.3.0]octane lignans: Syntheses of (±)-aptosi-mon, (±)-styraxin, (±)-asarinin, and (±)-pluv-iatilol
    • Stevens, D. R., and Whiting, D. A., Synthetic methods for (exo, exo)-and (exo-, endo)-2,6-diaryl-bicyclo[3.3.0]octane lignans: syntheses of (±)-aptosi-mon, (±)-styraxin, (±)-asarinin, and (±)-pluv-iatilol. Tetrahedron Lett., 27, 4629-4632 (1986).
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4629-4632
    • Stevens, D.R.1    Whiting, D.A.2
  • 3
    • 0033083666 scopus 로고    scopus 로고
    • Lignans, neolignans and related compounds
    • Ward, R. S., Lignans, neolignans and related compounds. Nat. Prod. Rep., 16, 75-96 (1999).
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 75-96
    • Ward, R.S.1
  • 4
    • 0006875845 scopus 로고
    • Lignans from Aegilops ovata L. Synthesis of a 2,4- and a 2,6-diaryl monoepoxy lignanolide
    • Copper, R., Gottlieb, H. E., Lavie, D., and Levy, E. C., Lignans from Aegilops ovata L. Synthesis of a 2,4- and a 2,6-diaryl monoepoxy lignanolide. Tetrahedron, 35, 861-868 (1979).
    • (1979) Tetrahedron , vol.35 , pp. 861-868
    • Copper, R.1    Gottlieb, H.E.2    Lavie, D.3    Levy, E.C.4
  • 5
    • 37049070735 scopus 로고
    • A new synthetic route to furofuranolid lignans via the intramolecular mukaiyama reaction
    • Stevens, D. R., Till, C. P., and Whiting, D. A., A new synthetic route to furofuranolid lignans via the intramolecular mukaiyama reaction. J. Chem. Soc. Perkin Trans. I, 185-190 (1992).
    • (1992) J. Chem. Soc. Perkin Trans. I , pp. 185-190
    • Stevens, D.R.1    Till, C.P.2    Whiting, D.A.3
  • 6
    • 37049083541 scopus 로고
    • Synthesis of 4,8-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0] octan-2-ones and determination of their relative configuration via long-range proton couplings
    • Quideau, S., and Ralph, J., Synthesis of 4,8-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0] octan-2-ones and determination of their relative configuration via long-range proton couplings. J. Chem. Soc. Perkin Trans. I, 653-659 (1993).
    • (1993) J. Chem. Soc. Perkin Trans. I , pp. 653-659
    • Quideau, S.1    Ralph, J.2
  • 7
    • 0031468007 scopus 로고    scopus 로고
    • New synthesis of 2,6-diaryl-4-oxo-3,7-dioxabicy-clo[3.3.0]octanes: Synthesis of (±)-styraxin
    • Yoshida, S., Ogiku, T., Ohmizu, H., and Iwasaki, T., New synthesis of 2,6-diaryl-4-oxo-3,7-dioxabicy-clo[3.3.0]octanes: synthesis of (±)-styraxin. Synthesis, 1475-1480 (1997).
    • (1997) Synthesis , pp. 1475-1480
    • Yoshida, S.1    Ogiku, T.2    Ohmizu, H.3    Iwasaki, T.4
  • 8
    • 0035812685 scopus 로고    scopus 로고
    • C-H insertion approach to the synthesis of endo, exo-furofura-nones: Synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin
    • Brown, R. C. D., Bataille, C. J. R., Bruton, G., Hinks, J. D., and Swain, N. A., C-H insertion approach to the synthesis of endo, exo-furofura-nones: synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin. J. Org. Chem., 66, 6719-6728 (2001).
    • (2001) J. Org. Chem. , vol.66 , pp. 6719-6728
    • Brown, R.C.D.1    Bataille, C.J.R.2    Bruton, G.3    Hinks, J.D.4    Swain, N.A.5
  • 9
    • 0009736326 scopus 로고
    • Biological activities of lignans
    • MacRae, W. D., and Towers, G. H. N., Biological activities of lignans. Phytochemistry, 23, 1207-1220 (1984).
    • (1984) Phytochemistry , vol.23 , pp. 1207-1220
    • Macrae, W.D.1    Towers, G.H.N.2
  • 10
    • 0004266767 scopus 로고
    • Cambridge University Press, Cambridge
    • Ayres, D. C., and Loike, J. D., Lignans. Cambridge University Press, Cambridge (1990).
    • (1990) Lignans
    • Ayres, D.C.1    Loike, J.D.2
  • 11
    • 0036653647 scopus 로고    scopus 로고
    • Synthesis of 1,2-oxygenated 6-arylfurofuran lignan: Stereoselective synthesis of (1S,2S,5R,6S)-1-hydrox-ysamin
    • Yamauchi, S., Bando, S., and Kinoshita, Y., Synthesis of 1,2-oxygenated 6-arylfurofuran lignan: stereoselective synthesis of (1S,2S,5R,6S)-1-hydrox-ysamin. Biosci. Biotechnol. Biochem., 66, 1495-1499 (2002).
    • (2002) Biosci. Biotechnol. Biochem. , vol.66 , pp. 1495-1499
    • Yamauchi, S.1    Bando, S.2    Kinoshita, Y.3
  • 12
    • 0002502996 scopus 로고    scopus 로고
    • Stereoselective syntheses of (-)-podorhizol lignan and its derivatives: Erythro and threo preferential aldol condensation of potassium enolate from g-butyrolactone with alkoxybenzaldehyde
    • Yamauchi, S., Machi, M., and Kinoshita, Y., Stereoselective syntheses of (-)-podorhizol lignan and its derivatives: erythro and threo preferential aldol condensation of potassium enolate from g-butyrolactone with alkoxybenzaldehyde. Biosci. Biotechnol. Biochem., 63, 1453-1462 (1999).
    • (1999) Biosci. Biotechnol. Biochem. , vol.63 , pp. 1453-1462
    • Yamauchi, S.1    Machi, M.2    Kinoshita, Y.3
  • 13
    • 0020449864 scopus 로고
    • Stereoselective reactions V. Design of the asymmetric synthesis of lignan lactones. Synthesis of optically active podorhizon and deoxypodorhizon by 1,3-asymmetric induction
    • Tomioka, K., Mizuguchi, H., and Koga, K., Stereoselective reactions V. Design of the asymmetric synthesis of lignan lactones. Synthesis of optically active podorhizon and deoxypodorhizon by 1,3-asymmetric induction. Chem. Pharm. Bull., 30, 4304-4313 (1982).
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 4304-4313
    • Tomioka, K.1    Mizuguchi, H.2    Koga, K.3
  • 14
    • 33947085164 scopus 로고
    • Chemistry of carbanions XXIII. Use of metal complexes to control the aldol condensation
    • House, H. O., Crumrine, D. S., Teranishi, A. Y., and Olmstead, H. D., Chemistry of carbanions XXIII. Use of metal complexes to control the aldol condensation. J. Am. Chem. Soc., 95, 3310-3324 (1973).
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3310-3324
    • House, H.O.1    Crumrine, D.S.2    Teranishi, A.Y.3    Olmstead, H.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.