Intramolecular Oxidative Phenol Coupling. II. A Biogenetic-Type Synthesis of (±)-Maritidine1

Journal of the American Chemical Society

Volumn 92, Issue 4, 1970, Pages 1090-1092

  Schwartz, Martin A ^a   Holton, Robert A ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000188114     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00707a074     Document Type: Article

References (16)

1. Previous paper: M. A. Schwartz, R. A. Holton, and S. W. Scott, J. Amer. Chem. Soc., 91, 2800 (1969).
2. For a comprehensive review, see W. C. Wildman, Alkaloids, 11, 387 (1968).
3. R. A. Abramovitch and S. Takahashi, Chem. Ind. (London), 1039 (1963);
4. B. Franck and H. J. Lubs, Angew. Chem. Intern. Ed. Engl, 7, 223 (1968);
5. B. Franck and H. J. Lubs, Ann., 720, 131 (1969).
6. D. H. R. Barton and G. W. Kirby, J. Chem. Soc., 806 (1962).
7. Reference 2, p 356;
8. G. G. DeAngelis and W. C. Wildman, Tetrahedron Lett., 729 (1969).
9. 5bThe hydroxyl group stereochemistry shown in 4 was assigned as a result of the present work (see later).
10. 3unless otherwise specified) using a Bruker HS-9 spectrometer; chemical shifts are expressed in parts per million downfield from tetramethylsilane and coupling constants in hertz.
11. D. H. R. Barton, G. W. Kirby, J. B. Taylor, and G. M. Thomas, J. Chem. Soc., 4545 (1963). We find that I can be conveniently prepared in 90% yield by in situ sodium borohydride reduction of the imine formed from isovanillin and tyramine.
12. A. Goosen, E. V. O. John, F. L. Warren, and K. C. Yates, J. Chem. Soc., 4038 (1961).
13. W. Rodionow, Bull. Soc. Chim. Fr., 39, 305 (1926).
14. We are very grateful to Professor W. C. Wildman for providing samples of oxomaritidine, maritidine, epicrinine, and crinine.
15. The same nmr behavior has been observed and explained for derivatives of haemanthamine and crinamine: R. D. Haugwitz, P. W. Jeffs, and E. Wenkert, J. Chem. Soc., 2001 (1965).
16. H. W. Whitlock, Jr., and G. L. Smith, J. Amer. Chem. Soc., 89, 3600 (1967).