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Volumn 38, Issue 23, 1999, Pages 3555-3559

Biomimetic explorations towards the bisorbicillinoids: Total synthesis of bisorbicillinol, bisorbibutenolide, and trichodimerol

Author keywords

Biomimetic synthesis; Bisorbicillinols; Dimerizations; Natural products; Trichodimerol

Indexed keywords

BISORBIBUTENOLIDE; BISORBICILLINOID DERIVATIVE; BISORBICILLINOL; NATURAL PRODUCT; TRICHODIMEROL; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

EID: 0033521220     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3555::AID-ANIE3555>3.0.CO;2-Z     Document Type: Article
Times cited : (81)

References (24)
  • 13
    • 0345628131 scopus 로고    scopus 로고
    • A previous proposal regarding the biosynthesis of bisvertinol (6) from sorbicillin postulates a different pathway, in which an initial epoxidation of sorbicillin followed by reduction and then dimerization and ketalization is believed to be involved.[7]
    • A previous proposal regarding the biosynthesis of bisvertinol (6) from sorbicillin postulates a different pathway, in which an initial epoxidation of sorbicillin followed by reduction and then dimerization and ketalization is believed to be involved.[7]
  • 15
    • 37049042129 scopus 로고
    • J. F. W. McOmie, M. S. Tute, J. Chem. Soc. 1958, 3226-3227. This method was found to be superior on larger scale to the procedure described by the Sartori group; see F. Bigi, G. Casiraghi, G. Casnati, S. Marchesi, G. Sartori, C. Vignali, Tetrahedron 1984, 40, 4081-4084.
    • (1958) J. Chem. Soc. , pp. 3226-3227
    • McOmie, J.F.W.1    Tute, M.S.2
  • 16
    • 0000521632 scopus 로고
    • J. F. W. McOmie, M. S. Tute, J. Chem. Soc. 1958, 3226-3227. This method was found to be superior on larger scale to the procedure described by the Sartori group; see F. Bigi, G. Casiraghi, G. Casnati, S. Marchesi, G. Sartori, C. Vignali, Tetrahedron 1984, 40, 4081-4084.
    • (1984) Tetrahedron , vol.40 , pp. 4081-4084
    • Bigi, F.1    Casiraghi, G.2    Casnati, G.3    Marchesi, S.4    Sartori, G.5    Vignali, C.6
  • 17
    • 0345196105 scopus 로고    scopus 로고
    • 13C NMR spectra of bisorbicillinol (1) and bisorbibutenolide (2)
    • 13C NMR spectra of bisorbicillinol (1) and bisorbibutenolide (2).
  • 18
    • 0344765632 scopus 로고    scopus 로고
    • The acetate 7a did not give any Diels-Alder product 1 when heated in benzene or in AcOH for several hours
    • The acetate 7a did not give any Diels-Alder product 1 when heated in benzene or in AcOH for several hours.
  • 21
    • 0000292659 scopus 로고
    • b) D. H. R. Barton, P. D. Magnus, J. C. Quinney, J. Chem. Soc. Perkin Trans. I 1975, 1610-1614; see also: E. Adler, K. Holmberg, Acta. Chem. Scand. Ser. B 1974, 28, 465-472.
    • (1974) Acta. Chem. Scand. Ser. B , vol.28 , pp. 465-472
    • Adler, E.1    Holmberg, K.2
  • 22
    • 0345196104 scopus 로고    scopus 로고
    • Attempts to induce 7a to react under Lewis acid catalysis conditions were also made. Interestingly, when 7a was exposed to TBSOTf or TMSOTf, 3 was the major product formed together with small amounts of 1. TBS = tert-butyldimethylsilyl, Tf = trifluormethanesulfonyl, TMS = trimethylsilyl
    • Attempts to induce 7a to react under Lewis acid catalysis conditions were also made. Interestingly, when 7a was exposed to TBSOTf or TMSOTf, 3 was the major product formed together with small amounts of 1. TBS = tert-butyldimethylsilyl, Tf = trifluormethanesulfonyl, TMS = trimethylsilyl.
  • 23
    • 0345628130 scopus 로고    scopus 로고
    • Trichodimerol (4) was unavailable to us for direct comparison
    • Trichodimerol (4) was unavailable to us for direct comparison.
  • 24
    • 0033523823 scopus 로고    scopus 로고
    • For the first synthesis of enantiomerically pure trichodimerol by dimerization of resolved acetate 7a, see D. Barnes-Seeman, E. J. Corey, Org. Lett. 1999, 1, 1503-1504.
    • (1999) Org. Lett. , vol.1 , pp. 1503-1504
    • Barnes-Seeman, D.1    Corey, E.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.