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Volumn 42, Issue 33, 2003, Pages 3961-3964

From rigidity to conformational flexibility: Macrocyclic templates derived from ansa-steroids

Author keywords

Conformations; Macrocycles; Ring expansions; Steroids

Indexed keywords

BIOSYNTHESIS; RIGIDITY;

EID: 0041317008     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351385     Document Type: Article
Times cited : (19)

References (30)
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    • e) S. L. Schreiber, Science 2000, 287, 1964-1969.
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    • note
    • About 500 compounds of type 4 have been synthesized so far mainly with carousel reactors. Solid-phase synthesis was also successfully established. All compounds were characterized by NMR spectroscopy and/or mass spectrometry.
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    • note
    • a) Detailed biological results including the inhibition of phosphatases will be published elsewhere;
  • 17
    • 0041936044 scopus 로고    scopus 로고
    • note
    • In the conformational analysis the conformer distribution was calculated by the Monte Carlo method in the Alter Conformation module of SPARTAN'02 with the MMFF force field. Conformers thus obtained were further refined at the HF/3-21G* level of theory. The final characterization by frequency calculation revealed that the conformers of lowest energy thus obtained are true minima on the corresponding potential energy surface.
  • 18
    • 0041434665 scopus 로고    scopus 로고
    • 2 by least squares. All non-hydrogen atoms could be refined anisotropically. In 5 three crystallographically independent molecules in the asymmetric unit and one disordered molecule of toluene were refined using distance restraints and restraints for the anisotropic temperature factors. All hydrogen atoms in both structures were placed in geometrically ideal positions and refined using the riding model, in which the methyl groups could rotate about their local threefold axes. The isotropic temperature factors of all hydrogen atoms are 1.2 and 1.5 times the size of the temperature factors of the corresponding heavy atoms (for 5 and 11, respectively). The absolute structure for both molecules could not be determined. CCDC-205757 (5) and -205756 (11) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 19
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    • note
    • 3 (142 mg, 0.54 mmol) was added, the cooling bath removed, and the reaction mixture stirred for 1 h. Chromatography on silica gel with hexane/ethyl acetate (9:1 to 4:1) yielded a mixture of 11 and 12 (90 mg), which was separated by preparative HPLC (see Table 1).
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    • Dissertation, Universität Hannover
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    • a) J. Mulzer, K. Schein, J. W. Bats, J. Buschmann, P. Luger, Angew. Chem. 1998, 110, 1625-1628; Angew. Chem. Int. Ed. 1998, 37, 1566-1569;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1566-1569
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    • SHELXS-96, program for structure solution
    • "SHELXS-96, Program for Structure Solution": G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
    • (1990) Acta Crystallogr. Sect. A , vol.46 , pp. 467-473
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.