Taxane diterpenes 3: Formation of the eight-membered B-ring by semi-pinacol rearrangement

Tetrahedron

Volumn 52, Issue 45, 1996, Pages 14147-14176

  Magnus, Philip ^a   Diorazio, Louis ^a   Donohoe, Timothy J ^a   Giles, Melvyn ^a   Pye, Philip ^a   Tarrant, James ^a   Thom, Stephen ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

OXY;

EID: 0030569280     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00865-4     Document Type: Article

References (25)

1. 1. Bauta, W. E.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T. J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J. G.; Thom. S.; Ujjainwalla, F. Tetrahedron, 1996, 52, 14081.
2. 2. Magnus, P.; Booth, J.; Diorazio, L.; Donohoe, T. G.; Lynch, V.; Magnus, N.; Mendoza, J.; Pye, P.; Tarrant, J. G. Tetrahedron, 1996, 52, 14103.
3. 3 ether III, followed by butyl lithium gave IV. So at least an intramolecular addition is feasible. Deprotection of I and conversion of the C-20 alcohol into the ether V, followed by treatment with t-butyl lithium gave the carbenoid cyclopropanation adduct VI (structure by X-ray). The reluctance of the compound I to undergo addition directed our efforts towards examining a semi-pinacol-type rearrangement in the top-half of the bicyclo[5.4.0]undecenone structure. (equation presented)
4. 4. Coveney, D. J. "The Semipinacol and Other Rearrangements", Comprehensive Organic Synthesis, Ed., Trost, B. M.; Fleming, I.; Pattenden, G. Vol. 3., p. 777. Pergamon Press, 1991.
5. 5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
6. 5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
7. 5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
8. 5. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
9. 6. Burness, D. M. Organic Syntheses, Wiley, New York, 1963, Collect. Vol. VII, p 649.
10. 7. Ho, T-L.; Sapp, S. G. Syn. Commun. 1983, 13, 207.
11. 8. Stiles, M.; Mayer, R. P. J. Am. Chem. Soc. 1959, 81, 1497.
12. 9. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergammon Press,1983, Vol. 1, p. 182. Gutsche, D. C.; Redmore, D. Carbocyclic Ring Expansion Reactions; Academic Press, New York, 1968.
13. 9. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergammon Press,1983, Vol. 1, p. 182. Gutsche, D. C.; Redmore, D. Carbocyclic Ring Expansion Reactions; Academic Press, New York, 1968.
14. 10. Griffith, W. P.; Ley, S.V. Aldrichimica Acta 1990, Vol. 23, No. 1.
15. 11. Magnus, P.; Ujjainwalla, F.; Westwood, N.; Lynch, V. Tetrahedron Letters, 1996, In Press. Swindell, C. S.; Patel, B. P.; deSolms, S. J. J. Org. Chem., 1987, 52, 2346. Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28 5275. Swindell, C. S.; Patel, B. P. J. Org. Chem. 1990, 55, 3.
16. 11. Magnus, P.; Ujjainwalla, F.; Westwood, N.; Lynch, V. Tetrahedron Letters, 1996, In Press. Swindell, C. S.; Patel, B. P.; deSolms, S. J. J. Org. Chem., 1987, 52, 2346. Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28 5275. Swindell, C. S.; Patel, B. P. J. Org. Chem. 1990, 55, 3.
17. 11. Magnus, P.; Ujjainwalla, F.; Westwood, N.; Lynch, V. Tetrahedron Letters, 1996, In Press. Swindell, C. S.; Patel, B. P.; deSolms, S. J. J. Org. Chem., 1987, 52, 2346. Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28 5275. Swindell, C. S.; Patel, B. P. J. Org. Chem. 1990, 55, 3.
18. 11. Magnus, P.; Ujjainwalla, F.; Westwood, N.; Lynch, V. Tetrahedron Letters, 1996, In Press. Swindell, C. S.; Patel, B. P.; deSolms, S. J. J. Org. Chem., 1987, 52, 2346. Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28 5275. Swindell, C. S.; Patel, B. P. J. Org. Chem. 1990, 55, 3.
19. 12. Williams, D. R.; Benbow, J. W.; Allen, E. E. Tetrahedron Lett. 1990, 31, 6769. Weeks, P. D.; Brennan, D. P.; Kuhla, D. E.; Elliot, M. L.; Watson, H. A.; Wlodecki, B.; Breitenbach, R. J. Org. Chem. 1980, 45, 1109. Gergiadis, M. P.; Couladouros, E. A.; Polissiou, M. G. J. Org. Chem. 1982, 47, 3054.
20. 12. Williams, D. R.; Benbow, J. W.; Allen, E. E. Tetrahedron Lett. 1990, 31, 6769. Weeks, P. D.; Brennan, D. P.; Kuhla, D. E.; Elliot, M. L.; Watson, H. A.; Wlodecki, B.; Breitenbach, R. J. Org. Chem. 1980, 45, 1109. Gergiadis, M. P.; Couladouros, E. A.; Polissiou, M. G. J. Org. Chem. 1982, 47, 3054.
21. 12. Williams, D. R.; Benbow, J. W.; Allen, E. E. Tetrahedron Lett. 1990, 31, 6769. Weeks, P. D.; Brennan, D. P.; Kuhla, D. E.; Elliot, M. L.; Watson, H. A.; Wlodecki, B.; Breitenbach, R. J. Org. Chem. 1980, 45, 1109. Gergiadis, M. P.; Couladouros, E. A.; Polissiou, M. G. J. Org. Chem. 1982, 47, 3054.
22. 13. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 44. Rosini, G.; Ballini, R., Synthesis 1988, 833.
23. 13. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 44. Rosini, G.; Ballini, R., Synthesis 1988, 833.
24. 14. Treatment of 50 with DBU gave a mixture which contains two unsaturated aldehydes, tentatively assigned the structures VII and VIII. The presence of VIII was indicated by a proton at δ 6.9 (dd); The formation of VIII indicates that the isomerization of the C-3/4 double bond into the C-4/5 position, as suggested in Scheme 5 is feasible, but under basic conditions no ring expansion was observed. (equation presented)
25. 15. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716.