Total synthesis of (-)-cylindrocyclophane a via a double Horner-Emmons macrocyclic dimerization event [2]

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4982-4983

  Hoye, Thomas R ^a   Humpai, Paul E ^a   Moon, Bongjin ^a  

^a University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYLINDROCYCLOPHANE A; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

CYCLIZATION; DIMERIZATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034709454     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000429q     Document Type: Letter

References (26)

1. (a) Moore, B. S.; Chen, J.-L.; Patterson, G. M. L.; Moore, R. E.; Brinen, L. S.; Kato, Y.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 4061.
2. (b) Moore, B. S.; Chen, J.-L.; Patterson, G. M. L.; Moore, R. E. Tetrahedron 1992, 48, 3001.
3. (c) Bobzin, S. C.; Moore, R. E. Tetrahedron 1993, 49, 7615.
4. (a) Keehn, P. M.; Rosenfeld, S. M., Eds. Cyclophanes; Academic Press: New York. 1983.
5. (b) Vogtle, F. Cyclophane Chemistry; Wiley: New York, 1993.
6. (c) For a summary of naturally occurring phanes, see Chapter 11 in ref 2b.
7. (a) Smith, A. B.; Kozmin, S. A.; Paone, D. V. J. Am. Chem. Soc. 1999, 121, 7423.
8. (b) A synthesis of cylindrocyclophane A from the Smith laboratory is described in the accompanying contribution.
9. Hoye, T. R.; Ye. Z.; Yao, L. J.; North, J. T. J. Am. Chem. Soc. 1996, 118, 12074.
10. Successful relevant macrocyclic dimerization reactions were reported (a) Hoye, T. R., Humpal, P. E. Presented at the 212th National Meeting of the American Chemical Society, Orlando, FL, August 1996; paper ORGN 173. (b) Humpal, P. E. Ph.D. Thesis, University of Minnesota, 1996.
11. Successful relevant macrocyclic dimerization reactions were reported (a) Hoye, T. R., Humpal, P. E. Presented at the 212th National Meeting of the American Chemical Society, Orlando, FL, August 1996; paper ORGN 173. (b) Humpal, P. E. Ph.D. Thesis, University of Minnesota, 1996.
12. Nichols, D. E.; Dyer, D. C. J. Med. Chem. 1977, 20, 299.
13. 1H NMR analysis of the corresponding Mosher esters. Mosher ester formation from 9 itself was complicated by both partial racemization and elimination, indicative of facile ionizalion to an allylic carbocation.
14. (a) Rathke, M. W.; Sullivan, D. F. Synth. Comm. 1973, 3, 67.
15. (b) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
16. 1H NMR analysis of the sec-phenethyl ester 12 and confirmed at the stage of primary alcohol 13 by analysis of its Mosher ester. The absolute configuration of the new benzylic stereocenter was assumed to be R based upon a chair-transition state for the Claisen rearrangement.
17. Baltzly, R. J. Am. Chem. Soc. 1952, 74, 4586.
18. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
19. 6 or of (ii) DBU and LiCl in D3CC≡N. The intermolecular olefination proceeded smoothly, but there was no observable change in the isomeric integrity of ZZ-24, even after each mixture was incubated for 27 h. It is therefore unlikely that the diene-dienoates 24 (or, we presume, 25) are equilibrating under either of these sets of Horner-Emmons olefination conditions. The mixture of dienoate isomers appears result from a kinetically rather than thermodynamically controlled event.
20. Axelrod, E. H.; Milne, G. M.; Van Tamelen, E. E. J. Am. Chem. Soc. 1970, 92, 2139.
21. (a) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1980, 45, 849.
22. (b) Nonacidic workup was required ai this step to avoid isomerization of the alkenes.
23. Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Org. Chem. 1982, 47, 5074-5083.
24. (a) Mechoulam, R.; Gaoni, Y. J. Am. Chem. Soc. 1965, 87, 3273, wherein reference is made to the earlier unpublished use and recommendation of this method for cleavage of dimethyl resorcinols by Professor G. Ourisson.
25. (b) Meerwein, H. Houben-Weyl, Methoden der Organische Chemie; Müller, E., Ed.; George Thieme Verlag: Stuttgart, 1964; Vol. VI, pp 160-164.
26. 3/EtSH, conditions that were not successful in the case of conversion of 29 to 1A.