Natural Products Chemistry: Volume 1 by Koji Nakanishi

By Koji Nakanishi

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R. Battersby,loganin R. T. Brown, R. S. Kapil, J. A. Martin, A. O. Plunkett, Chem. , 888 (1966); A. R. Battersby, R. S. Kapil, J. A. Martin, L. , 133 (1968). 2) P. Loew, D. Arigoni, Chem. , 137 (1968). 3) A. R. Battersby, E. S. Hall, R. Southgate, / . Chem. Soc. C, 721 (1969). 4) S. Escher, P. Loew, D. Arigoni, Chem. , 823 (1970). 5) A. R. Battersby, S. H. Brown, T. G. Payne, Chem. , 827 (1970). 6) A. R. Battersby, A. R. Burnett, P. G. Parsons, Chem. , 826 (1970). 7) H. Inouye, S. Ueda, Y. Aoki, Y.

F. Mason, G. W. Vane, / . Chem. Soc, B, 370 (1966); S. F. Mason, K. Schofield, R. J. Wells, J. S. Whitehurst, G. W. Vane, Tetr. , 137 (1967). Bb t-^e "L. ■L. 34 32 Y Λ O 36 Benzoate rule (Brewster)38) When benzoates are prepared from secondary alcohols with absolute configurations 37 or 38, a positive shift as compared to the carbinol is observed in the D-line rotation. This simple rule has been applied successfully to numerous natural products. However, here again it should be cautioned that the results rely on [a]D.

Aliph. sec-, ter/-amine: C-CJN-cjc '* aliph. aldehyde: Γ Λ fc ß^C^ ^Η ß-cleavage with (H · ) transfer from γ-C (McLafTerty rearrangement): 4 4 , 5 8 , 7 2 , . . 45) K. Biemann, Mass Spectrometry, McGraw-Hill, 1962. 46) F. W. McLafferty, Mass Spectrometry of Organic Ions, Academic Press, 1963. 47) H. Budzikiewicz, C. Djerassi, D. H. Williams, Interpretation of Mass Spectra of Organic Compounds, and Structure Elucidation of Natural Products by Mass Spectrometry, vol. I and vol. II, Holden-Day, 1964.

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