Stereochemistry of epoxidation of some caryophyllenols

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 1965-1969

  Collado, Isidro G ^a   Hanson, James R ^b   Hitchcock, Peter B ^b   Macías Sánchez, Antonio J ^b  

^a UNIVERSITY OF CÁDIZ   (Spain)

^b UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARYOPHYLLENE DERIVATIVE; EPOXIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030917809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9617979     Document Type: Article

References (19)

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12. The most stable conformation (PM3 parametrization) of compound 8 shows a value of 59.7° for the dihedral angle formed by atoms α, β, γ, and δ. On the other hand, there is an energy minimum for dihedral angle value of 45° in intermediate B (see Figure 1). So, it seems reasonable to consider the conformation shown in Figure 1 as the preferred structure for a 1,2 H shift in intermediate B.
13. Most stable conformers for exo-C-5 substituent were calculated using the MOPAC 6.0 program (ref 7). Calculated heats of formation of the appropriate conformations of compounds 3-5 were -36.512, -41.685, and -29.202 kcal/mol, respectively.
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19. The author has deposited atomic coordinates for 11b and 14 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.