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Volumn 109, Issue 10, 1987, Pages 3017-3024

Enantiospecific Total Synthesis of the Sesquiterpene Antibiotics (-)-Punctatin A and (+)-Punctatin D

Author keywords

[No Author keywords available]

Indexed keywords

PUNCTATIN A; PUNCTATIN D; UNCLASSIFIED DRUG;

EID: 0023262041     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00244a025     Document Type: Article
Times cited : (83)

References (19)
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    • Five additional metabolites that co-occur with 1 have been assigned the names punctatin BF and structurally characterized: Poyser, J. P.; Edwards, R. L.; Anderson, J. R.; Hursthouse, M. B.; Walker, N. P. C.; Sheldrick, G. M.; Whalley, A. J. S. J. Antibiot. 1986, 39, 167.
    • Five additional metabolites that co-occur with 1 have been assigned the names punctatin BF and structurally characterized: Anderson, J. R.; Edwards, R. L.; Fraer, A. A.; Mabelix, R. P.; Poyser, J. P.; Spencer, H.; Whalley, A. J. S. J. Chem. Soc., Chem. Commun. 1984, 917. Poyser, J. P.; Edwards, R. L.; Anderson, J. R.; Hursthouse, M. B.; Walker, N. P. C.; Sheldrick, G. M.; Whalley, A. J. S. J. Antibiot. 1986, 39, 167.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 917
    • Anderson, J.R.1    Edwards, R.L.2    Fraer, A.A.3    Mabelix, R.P.4    Poyser, J.P.5    Spencer, H.6    Whalley, A.J.S.7
  • 3
    • 26644440941 scopus 로고
    • Care should be exercised not to confuse punctatin A with punctatin, a germacranolide obtained from Liatris punctata Hook (). This substance was later renamed punc-taliatrin (Herz, W.; Wahlberg, I. Phytochemistry 1974, 13, 315). An even earlier use of the name for a group of homoisoflavones has turned up (Heller, W.; Tamm, C. Prog. Chem. Org. Nat. Prods. 1981, 40, 105). We have been
    • Care should be exercised not to confuse punctatin A with punctatin, a germacranolide obtained from Liatris punctata Hook (Herz, W.; Wahlberg, I Phytochemistry 1973, 12, 1421). This substance was later renamed punc-taliatrin (Herz, W.; Wahlberg, I. Phytochemistry 1974, 13, 315). An even earlier use of the name for a group of homoisoflavones has turned up (Heller, W.; Tamm, C. Prog. Chem. Org. Nat. Prods. 1981, 40, 105). We have been
    • (1973) Phytochemistry , vol.12 , pp. 1421
    • Herz, W.1    Wahlberg, I.2
  • 5
    • 0345435985 scopus 로고
    • Fleming, I.; Long, W. E. J. Am. Chem. Soc. 1976, 14. Singh, S.; Usha, G.; Tung, C. H. ; Turro, N. J.; Ramamurthy, V. J. Org. Chem. 1986, 51, 941 and relevant references cited in these papers.
    • Fleming, I.; Kemp-Jones, A. V.; Long, W. E.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 2 1976, 7. Fleming, I.; Long, W. E. J. Am. Chem. Soc. 1976, 14. Singh, S.; Usha, G.; Tung, C. H. ; Turro, N. J.; Ramamurthy, V. J. Org. Chem. 1986, 51, 941 and relevant references cited in these papers.
    • (1976) J. Chem. Soc., Perkin Trans. 2 , pp. 7
    • Fleming, I.1    Kemp-Jones, A.V.2    Long, W.E.3    Thomas, E.J.4
  • 6
    • 85022725538 scopus 로고
    • Still, W. C.; Mitra, A. J. Chem. Soc., Perkin Trans. 2 1978, 100, 1927.
    • Still, W. C. J. Am. Chem. Soc. 1978, 100, 1480. Still, W. C.; Mitra, A. J. Chem. Soc., Perkin Trans. 2 1978, 100, 1927.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 1480
    • Still, W.C.1
  • 12
    • 20444433122 scopus 로고
    • Fraser-Reid, B.; Holder, N. L.; Hicks, D. R.; Walker, D. L. Can. J. Chem. 1977, 55, 3978 and relevant references cited in these papers.
    • Fitzsimmons, B. J.; Fraser-Reid, B. J. Am. Chem. Soc. 1979, 101, 6123. Fraser-Reid, B.; Holder, N. L.; Hicks, D. R.; Walker, D. L. Can. J. Chem. 1977, 55, 3978 and relevant references cited in these papers.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6123
    • Fitzsimmons, B.J.1    Fraser-Reid, B.2
  • 16
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    • See, for example: Lewis, F. D.; Hilliard, T. A. J. Am. Chem. Soc. 1972, 94, 3852. Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. Turro, N. J.; Wan P. Tetrahedron Lett. 1984, 3655.
    • See, for example: Yang, N. C.; Thap, D. M. Tetrahedron Lett. 1966, 3671. Lewis, F. D.; Hilliard, T. A. J. Am. Chem. Soc. 1972, 94, 3852. Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. Turro, N. J.; Wan P. Tetrahedron Lett. 1984, 3655.
    • (1966) Tetrahedron Lett. , pp. 3671
    • Yang, N.C.1    Thap, D.M.2
  • 17
    • 33947312570 scopus 로고
    • Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; McGrath, J. M.; Zepp, R. G. Tetrahedron Lett. 1972, 94, 7506. Wagner, P. J.; McGrath, J. M. Tetrahedron Lett. 1972, 94, 3849. Padwa, A.; Alexander, E.; Niemczyk, M. Tetrahedron Lett. 1969,91, 456. Sauers, R. R.; Gorodetsky, M.; Whittle, J. A.; Hu, C. K. Tetrahedron Lett. 1971, 93, 5520. Lewis, F. D.; Johnson, R. W.; Ruden, R. A. Tetrahedron Lett. 1972, 94, 4292. Gagosian, R. B.; Dalton, J. C.; Turro, N. J. Tetrahedron Lett. 1970, 92, 4752.
    • Wagner, P. J.; Kemppainen, A. E. J. Am. Chem. Soc. 1968, 90, 5896. Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; McGrath, J. M.; Zepp, R. G. Tetrahedron Lett. 1972, 94, 7506. Wagner, P. J.; McGrath, J. M. Tetrahedron Lett. 1972, 94, 3849. Padwa, A.; Alexander, E.; Niemczyk, M. Tetrahedron Lett. 1969,91, 456. Sauers, R. R.; Gorodetsky, M.; Whittle, J. A.; Hu, C. K. Tetrahedron Lett. 1971, 93, 5520. Lewis, F. D.; Johnson, R. W.; Ruden, R. A. Tetrahedron Lett. 1972, 94, 4292. Gagosian, R. B.; Dalton, J. C.; Turro, N. J. Tetrahedron Lett. 1970, 92, 4752.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5896
    • Wagner, P.J.1    Kemppainen, A.E.2


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