Total synthesis of (±)-biphyscion

Organic Letters

Volumn 1, Issue 4, 1999, Pages 671-672

  Hauser, Frank M ^a   Gauuan, Polivina Jolicia F ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,7' BIPHYSCION; 7,7'-BIPHYSCION; ANTHRAQUINONE DERIVATIVE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTHRAQUINONES; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0033606871     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990758r     Document Type: Article

References (28)

1. (a) For an extensive list on naturally occurring bianthraquinones, see: ; Academic Press: New York, 1971; Vol. I, Chapter 5.
2. (b) Thompson, R. H. Naturally Occurring Quinones, 2nd ed.; Chapman and Hall: New York. 1987; Vol. 3, Chapter 3.
3. 6 affords an unnatural 4,7′-linked bianthraquinone (30%) and a trace (0.28%) of the 5,5-linked bianthraquinone, skyrin: Kato, T.; Hozumi, T. Chem. Pharm. 1972, 20, 1574.
4. 6 affords an unnatural 4,7′-linked bianthraquinone (30%) and a trace (0.28%) of the 5,5-linked bianthraquinone, skyrin: Kato, T.; Hozumi, T. Chem. Pharm. 1972, 20, 1574.
5. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
6. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
7. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
8. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
9. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
10. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
11. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. For use of this reaction in natural products syntheses, see: Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 106, 1098. Hauser, F. M.; Prasanna, S. Tetrahedron 1984, 40, 4711. Hauser, F. M.; Chakrapani, S.; Ellenberger, W. P. J. Org. Chem. 1991, 56, 5248. Hauser, F. M.; Tommassi, R. A. J. Org. Chem, 1991, 56, 5758. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722. Hauser, F. M.; Xu, Y. Org. Lett. In press.
12. Gluchoff, K.; Arpin, N.; Dangy-Caye, M.; Lebreton, P.; Steglich, W.; Töpfer, E.; Pourrat, M.; Regerat, F.; Deruaz, D. C. R. Seances Acad. Sci., Ser. 3 1972, 274, 1739. Steglich, W.; Töpfer-Petersen, E.; Reininger, W.; Gluchoff, K.; Arpin, N. Phytochemistry 1972, 11, 3299.
13. Gluchoff, K.; Arpin, N.; Dangy-Caye, M.; Lebreton, P.; Steglich, W.; Töpfer, E.; Pourrat, M.; Regerat, F.; Deruaz, D. C. R. Seances Acad. Sci., Ser. 3 1972, 274, 1739. Steglich, W.; Töpfer-Petersen, E.; Reininger, W.; Gluchoff, K.; Arpin, N. Phytochemistry 1972, 11, 3299.
14. The details of this study will be published elsewhere.
15. Ullman, F.; Bielecki, J. Chem. Ber 1901, 34, 2174. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Fanta, P. E. Synthesis 1974, 9. Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
16. Ullman, F.; Bielecki, J. Chem. Ber 1901, 34, 2174. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Fanta, P. E. Synthesis 1974, 9. Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
17. Ullman, F.; Bielecki, J. Chem. Ber 1901, 34, 2174. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Fanta, P. E. Synthesis 1974, 9. Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
18. Ullman, F.; Bielecki, J. Chem. Ber 1901, 34, 2174. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Fanta, P. E. Synthesis 1974, 9. Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
19. Ullman, F.; Bielecki, J. Chem. Ber 1901, 34, 2174. Bringman, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977. Fanta, P. E. Synthesis 1974, 9. Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
20. Hauser, F. M.; Rhee, R. P.; Weinreb, S. M.; Dodd, J. H. Synthesis 1980, 73.
21. 3, the yield was only 70%.
22. The diastereoisomeric ratio was unaltered during oxidation.
23. 13C spectra indicating that all the protons and all the carbons were different.
24. Hauser, F. M.; Takeuchi, C.; Yin, H.; Corlett, S. A. J. Org. Chem. 1994, 59, 258-259.
25. Arkley, V.; Attenburrow, G. I.; Gregory, G. I.; Walker, T. J. Chem. Soc. 1962, 1260. Greaory, G. I.; Holton, P. J.; Robinson, H.; Walker, T. J. Chem. Soc. 1962. 1269. Bycroft, B. W.; Holton, P. J.; Roberts, J. C. J. Chem. Soc. 1963, 4868. Hauser, F. M.; Sengupta, D.; Corlett, S. A. J. Org. Chem. 1994, 59, 1967.
26. Arkley, V.; Attenburrow, G. I.; Gregory, G. I.; Walker, T. J. Chem. Soc. 1962, 1260. Greaory, G. I.; Holton, P. J.; Robinson, H.; Walker, T. J. Chem. Soc. 1962. 1269. Bycroft, B. W.; Holton, P. J.; Roberts, J. C. J. Chem. Soc. 1963, 4868. Hauser, F. M.; Sengupta, D.; Corlett, S. A. J. Org. Chem. 1994, 59, 1967.
27. Arkley, V.; Attenburrow, G. I.; Gregory, G. I.; Walker, T. J. Chem. Soc. 1962, 1260. Greaory, G. I.; Holton, P. J.; Robinson, H.; Walker, T. J. Chem. Soc. 1962. 1269. Bycroft, B. W.; Holton, P. J.; Roberts, J. C. J. Chem. Soc. 1963, 4868. Hauser, F. M.; Sengupta, D.; Corlett, S. A. J. Org. Chem. 1994, 59, 1967.
28. Arkley, V.; Attenburrow, G. I.; Gregory, G. I.; Walker, T. J. Chem. Soc. 1962, 1260. Greaory, G. I.; Holton, P. J.; Robinson, H.; Walker, T. J. Chem. Soc. 1962. 1269. Bycroft, B. W.; Holton, P. J.; Roberts, J. C. J. Chem. Soc. 1963, 4868. Hauser, F. M.; Sengupta, D.; Corlett, S. A. J. Org. Chem. 1994, 59, 1967.