Structure and reactivity of a chiral cyclononadienone

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1882-1885

  Zhang, Yue ^a   Lotesta, Stephen D ^a   Emge, Thomas J ^a   Williams, Lawrence J ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Caryophylloids; Nine membered rings; Synthesis; Xenicanes

Indexed keywords

CYCLOALKANE DERIVATIVE; CYCLONONADIENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; CYCLIZATION; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 61749099597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.017     Document Type: Article

References (31)

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18. Molecular modeling suggests that 15 is highly constrained and that the (HO)CCCO(Ts) torsion angle is 139° (see Ref. 16).
19. This compound was characterized by single crystal X-ray diffraction. Crystallographic data for compound 17, 19, and 22 have been deposited with the Cambridge Crystallographic Data Center, Nos. CCDC 712607 (17), CCDC 712606 (19), and CCDC 712605 (22). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.Uk).
20. Molecular modeling suggests that 18 is more highly constrained than 15, and the (HO)CCCO(Ts) torsion angle for 18 is better suited for fragmentation (165°) (see Ref. 16).
21. NOSY analysis shows the olefin protons as proximal, cf. 3c.
22. Calculations used (DFT-B3LYP 6-31G(d, p)). (a) All structures were fully optimized by analytical gradient methods using the Gaussian 03 suites,. Frisch M.J., Trucks G.W., Schlege H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., et al. Gaussian 03, Revision E.01 (2004), Gaussian, Wallingford, CT
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28. Although these Lewis acids failed, trityl perchlorate was effective at promoting conjugate addition to this enone (Ref. 3c).
29. Assignments of 20 and 21 were based on the enone proton signals (5.88 ppm for cis, 20, and 6.72 ppm for trans, 21) by analogy to:. Taber D.F., Jiang Q., Chen B., Zhang W., and Campbell C.L. J. Org. Chem. 67 (2002) 4821-4827
30. For example, reduction of 1 (in one instance enone of 60% ee was used) provided 22 from which 23 was prepared as a mixture of diastereomers (dr = 4:1, corresponding to 60% ee of 22). Crystallographic structure determination of 22 revealed this material to be a disordered solid composed of both enantiomers (see Ref. 13).
31. +; calcd: 231.