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Volumn 64, Issue 48, 2008, Pages 10896-10905

Substituent effects in the transannular cyclizations of germacranes. Synthesis of 6-epi-costunolide and five natural steiractinolides

Author keywords

[No Author keywords available]

Indexed keywords

6 EPICOSTUNOLIDE; EUDESMANOLIDE 9; EUDESMANOLIDE DERIVATIVE; GERMACRANOLIDE DERIVATIVE; GERMACRANONE 5; GUAIANOLIDE DERIVATIVE; SESQUITERPENE; STEIRACTINOLIDE DERIVATIVE; STEIRACTNOLIDE 12; UNCLASSIFIED DRUG;

EID: 53649110406     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.017     Document Type: Article
Times cited : (30)

References (41)
  • 3
    • 36349020798 scopus 로고    scopus 로고
    • and previous references of this series
    • Fraga B.M. Nat. Prod. Rep. 24 (2007) 1350-1381 and previous references of this series
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 1350-1381
    • Fraga, B.M.1
  • 17
    • 53649105306 scopus 로고    scopus 로고
    • Cauwet-Marc, A. M.; Carbonnier, J. Actes du 2eme Symposium International sur les Ombelliferes. Centre Universitaire de Perpignan: Perpignan, 1977.
    • Cauwet-Marc, A. M.; Carbonnier, J. Actes du 2eme Symposium International sur les Ombelliferes. Centre Universitaire de Perpignan: Perpignan, 1977.
  • 20
    • 53649085474 scopus 로고    scopus 로고
    • (E,E)-Germacradienes can adopt several conformations from which those denoted as UU, UD, DU and DD are the most stable ones. U (up) and D (down) refers to the orientation of the C-14 and C-15 methyl groups. See:
    • (E,E)-Germacradienes can adopt several conformations from which those denoted as UU, UD, DU and DD are the most stable ones. U (up) and D (down) refers to the orientation of the C-14 and C-15 methyl groups. See:
  • 22
    • 53649096423 scopus 로고    scopus 로고
    • Samek uses a different notation for the conformations of germacranes, see:
    • Samek uses a different notation for the conformations of germacranes, see:
  • 24
    • 53649110477 scopus 로고    scopus 로고
    • For some other references about conformational equilibria and cyclization of germacranes, see:
    • For some other references about conformational equilibria and cyclization of germacranes, see:
  • 30
    • 53649094044 scopus 로고    scopus 로고
    • note
    • At this point, we observed that in some runs, partial racemization of germacranone 5 could occur. The presence of pyridine is necessary to avoid the cyclization to the corresponding eudesmanes, but at the same time it may provoke the racemization through inversion of the configuration of C-7. For this reason, from 5 to 18 the values of the optical rotations are not supplied. This fact is not observed in the synthesis of 19 (vide infra), since C-7 is not allylic.
  • 32
    • 53649102725 scopus 로고    scopus 로고
    • note
    • A steiractinolide is a 5βH,10αMe-eudesmanolide.
  • 33
    • 84982401424 scopus 로고
    • Compounds 9 and 10 are first described in
    • Compounds 9 and 10 are first described in. Bohlmann F., Jakupovic J., and Lonitz M. Chem. Ber. 110 (1977) 301-314
    • (1977) Chem. Ber. , vol.110 , pp. 301-314
    • Bohlmann, F.1    Jakupovic, J.2    Lonitz, M.3
  • 34
    • 0001361233 scopus 로고
    • Their absolute stereochemistry is corrected in
    • Their absolute stereochemistry is corrected in. Bohlmann F., Jakupovic J., and Schuster A. Phytochemistry 22 (1983) 1637-1644
    • (1983) Phytochemistry , vol.22 , pp. 1637-1644
    • Bohlmann, F.1    Jakupovic, J.2    Schuster, A.3
  • 36
    • 53649093860 scopus 로고    scopus 로고
    • note
    • Nevertheless, treatment of its epimer 4 under the same epoxidation conditions is totally regioselective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.