Biogenetically Modeled Syntheses of Heptaacetate Metabolites. Alternariol and Lichexanthone

Journal of the American Chemical Society

Volumn 99, Issue 5, 1977, Pages 1631-1637

  Harris, Thomas M ^a   Hay, James V ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNARIOL;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; LICHEXANTHONE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THEORETICAL STUDY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0017398771     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00447a058     Document Type: Article

References (28)

1. For reviews, see A. J. Birch, Fortschr. Chem. Org. Naturst., 14, 186 (1957), and J. H. Richards and J. B. Hendrickson, “The Biosynthesis of Steroids, Terpenes, and Acetogenins”, W. A. Benjamin, New York, N.Y., 1964.
2. These studies have been summarized in a review: T. M. Harris, C. M. Harris, and K. B. Hindley, Fortschr. Chem. Org. Naturst., 31, 217 (1974).
3. Y. Asahina and H. Nogami, Bull. Chem. Soc. Jpn., 17, 202 (1942).
4. Noteworthy examples of related metabolites include griseofulvin, griseo-phenones, and griseoxanthones; see J. F. Grove, Fortschr. Chem. Org. Naturst., 22, 203 (1964).
5. H. Raistrick, C. E. Stickings, and R. Thomas, Biochem. J., 55, 421 (1953).
6. For a preliminary communication, see J. V. Hay and T. M. Harris, J. Chem. Soc., Chem. Commun., 953 (1972).
7. T. T. Howarth, G. P. Murphy, and T. M. Harris, J. Am. Chem. Soc., 91,517 (1969).
8. The migration or loss of o-O-benzyl groups in the formation of 16, 21, and 24 is not fully understood. Comparable reactions of the o-O-methyl group were not observed during the synthesis of 8. Other anomalous reactions of benzyl ethers have been observed: B. E. Cross and L. J. Zammitt, Tetrahedron, 32, 1587 (1976).
9. T. M. Harris and R. L. Carney, J. Am. Chem. Soc., 89, 6734 (1967);
10. T. T. Howarth and T. M. Harris, J. Am. Chem. Soc., 93, 2506 (1971);
11. T. M. Harris, T. T. Howarth, and R. L. Carney, J. Am. Chem. Soc., 93, 2511 (1971).
12. T. M. Harris and M. P. Waohter, Tetrahedron, 26, 5255 (1970).
13. Scott has reported a biogenetically modelled synthesis of a symmetrically substituted xanthone but an approach to the alternariol ring system was unsuccessful: A. I. Scott, D. G. Pike, J. J. Ryan, and H. Guilford, Tetrahedron, 27, 3051 (1971);
14. A. I. Scott, H. Guilford, J. J. Ryan, and D. Skingle, Tetrahedron, 27, 3025 (1971).
15. A closely related pathway involves closure of the second ring prior to aromatization of the first. An ester of i would be an intermediate in thisprocess. Several examples of undehydrated aldol cyclization products have been found in nature: L. K. Dalton and J. A. Lamberton, Aust. J. Chem., 11, 46 (1958);
16. D. L. Dreyer, I. Arai, C. D. Bachman, W. R. Anderson, R. G. Smith, and G. D. Daves, J. Am. Chem. Soc., 97, 4985 (1975), and references cited therein.
17. W. J. McMaster, A. I. Scott, and S. Trippett, J. Chem. Soc., 4628 (1960);
18. A. Rhodes, B. Boothroyd, M. P. McGonagle, and G. A. Somerfield, Biochem. J. 81, 2(1961);A.Rhodes, Prog. Ind. Microbiol., 4, 165 (1963);
19. M. Tanabe and G. Detre, J. Am. Chem. Soc., 88, 4515 (1966).
20. A. J. Birch, Proc. Chem. Soc., London, 3 (1962).
21. C. M. Harris, J. S. Roberson, and T. M. Harris, J. Am. Chem. Soc., 98, 5380 (1976).
22. J. Santesson, Acta Chem. Scand., 22, 1698 (1968).
23. O. Hesse, Justus Liebigs Ann. Chem., 117, 297 (1861); 139, 22 (1866).
24. J. Herzig, F. Wenzel, and P. Kurzweil, Monatsh. Chem., 24, 898 (1903).
25. P. K. Grover, G. D. Shah, and R. C. Shah, J. Sci. Ind. Res., Sect. B, 15, 629 (1956).
26. T. Bruun, Acta Chem. Scand., 19, 1677 (1965).
27. S. M. Sethna and R. C. Shah, J. Indian Chem. Soc., 17, 211 (1940).
28. S. Iguchi and N. Utsugi, J. Pharm. Soc. Jpn., 73, 1290 (1953).