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Volumn 118, Issue 39, 1996, Pages 9249-9254

Stereochemistry and reactions of presilphiperfolanol: A branch point marker in triquinane sesquiterpene biogenesis

Author keywords

[No Author keywords available]

Indexed keywords

PRESILPHIPERFOLANOL; SESQUITERPENE; UNCLASSIFIED DRUG;

EID: 0029903530     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961582g     Document Type: Article
Times cited : (55)

References (33)
  • 1
    • 0001024939 scopus 로고
    • Bohlmann, F.; Zdero, C.; Jakupovic, J.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 2239-2244. Note Added in Proof. The isolation and total synthesis of presilphiperfolan-9-ol (formally derived from 4) have recently been reported: Marco, J. A.; Sanz-Cervera, J. F.; Morante, M. D.; García-Lliso, V.; Vallès-Xirau; Jakupovic, J. Phytochemistry 1996, 41, 837-844. Weyerstahl, P.; Marschall, H.; Schulze, M.; Schwope, I. Liebigs Ann. Chem. 1996, 799-807.
    • (1981) Phytochemistry , vol.20 , pp. 2239-2244
    • Bohlmann, F.1    Zdero, C.2    Jakupovic, J.3    Robinson, H.4    King, R.M.5
  • 2
    • 0030039072 scopus 로고    scopus 로고
    • Bohlmann, F.; Zdero, C.; Jakupovic, J.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 2239-2244. Note Added in Proof. The isolation and total synthesis of presilphiperfolan-9-ol (formally derived from 4) have recently been reported: Marco, J. A.; Sanz-Cervera, J. F.; Morante, M. D.; García-Lliso, V.; Vallès-Xirau; Jakupovic, J. Phytochemistry 1996, 41, 837-844. Weyerstahl, P.; Marschall, H.; Schulze, M.; Schwope, I. Liebigs Ann. Chem. 1996, 799-807.
    • (1996) Phytochemistry , vol.41 , pp. 837-844
    • Marco, J.A.1    Sanz-Cervera, J.F.2    Morante, M.D.3    García-Lliso, V.4    Vallès-Xirau5    Jakupovic, J.6
  • 3
    • 33749023316 scopus 로고    scopus 로고
    • Bohlmann, F.; Zdero, C.; Jakupovic, J.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 2239-2244. Note Added in Proof. The isolation and total synthesis of presilphiperfolan-9-ol (formally derived from 4) have recently been reported: Marco, J. A.; Sanz-Cervera, J. F.; Morante, M. D.; García-Lliso, V.; Vallès-Xirau; Jakupovic, J. Phytochemistry 1996, 41, 837-844. Weyerstahl, P.; Marschall, H.; Schulze, M.; Schwope, I. Liebigs Ann. Chem. 1996, 799-807.
    • (1996) Liebigs Ann. Chem. , pp. 799-807
    • Weyerstahl, P.1    Marschall, H.2    Schulze, M.3    Schwope, I.4
  • 4
    • 10244227007 scopus 로고    scopus 로고
    • note
    • Semisystematic names for presilphiperfolane, silphiperfolane, and silphinane derivatives together with a common positional numbering scheme are used in this paper. Systematic IUPAC and Chemical Abstracts names are given in the abstract.
  • 10
    • 37049110241 scopus 로고
    • The co-occurrence of isocomene, modhephene, and caryophyllene in Isocoma Wrightii and the liklihood of their biogenetic relationship have been noted by Zalkow and co-workers in the initial discovery of these novel triquinane sesquiterpenes: (a) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D.; Bertrand, J. A. J. Chem. Soc., Chem. Commun. 1977, 456-457. (b) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D. J. Chem. Soc., Chem. Commun. 1978, 420-421.
    • (1977) J. Chem. Soc., Chem. Commun. , pp. 456-457
    • Zalkow, L.H.1    Harris III, R.N.2    Van Derveer, D.3    Bertrand, J.A.4
  • 11
    • 0344397650 scopus 로고
    • The co-occurrence of isocomene, modhephene, and caryophyllene in Isocoma Wrightii and the liklihood of their biogenetic relationship have been noted by Zalkow and co-workers in the initial discovery of these novel triquinane sesquiterpenes: (a) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D.; Bertrand, J. A. J. Chem. Soc., Chem. Commun. 1977, 456-457. (b) Zalkow, L. H.; Harris, R. N., III; Van Derveer, D. J. Chem. Soc., Chem. Commun. 1978, 420-421.
    • (1978) J. Chem. Soc., Chem. Commun. , pp. 420-421
    • Zalkow, L.H.1    Harris III, R.N.2    Van Derveer, D.3
  • 12
    • 0002642584 scopus 로고
    • For reviews, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152, 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1979) Top. Curr. Chem. , vol.79 , pp. 41-152
    • Paquette, L.A.1
  • 13
    • 20644435283 scopus 로고
    • For reviews, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152, 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1984) Top. Curr. Chem. , vol.119 , pp. 1-147
  • 14
    • 0004154187 scopus 로고
    • Springer-Verlag: Berlin
    • For reviews, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152, 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1987) Polyquinane Chemistry
    • Paquette, L.A.1    Doherty, A.M.2
  • 19
    • 10244225544 scopus 로고    scopus 로고
    • note
    • CD2Cl2 37.6 (d, C9), 34.6 (t, C10), 36.4 (q, C12), 28.6(q, C14, 21.6 (q, C15).
  • 23
    • 10244234359 scopus 로고    scopus 로고
    • note
    • 12; colorless; cell parameters, a = b = 8.211(2), c = 58.657(13); z = 8; R1 = 0.1243; GOF = 1.10.
  • 25
    • 0000482183 scopus 로고
    • Lithium-ethylenediamine reduction of 4,5,6,7-tetrahydroindane epoxide afforded cis- and trans-8-hydrindanols in a 58:42 ratio; see: Benkeser, R. A.; Rappa, A.; Wolsieffer, L. A. J. Org. Chem. 1986, 51, 3391-3393.
    • (1986) J. Org. Chem. , vol.51 , pp. 3391-3393
    • Benkeser, R.A.1    Rappa, A.2    Wolsieffer, L.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.