Synthesis of (±)-Cylindricines A, D, and E

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5630-5633

  Snider, Barry B ^a   Liu, Tao ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000932594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970536b     Document Type: Article

References (21)

1. Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645-8656.
2. Li, C.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355-1361.
3. Li, C.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955-965.
4. Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Tetrahedron Lett. 1997, 38, 363-364.
5. (a) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
6. (b) Broka, C. A.; Eng, K. K. J. Org. Chem. 1986, 51, 5043-5045.
7. Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
8. (b) Blough, B. E.; Mascarella, S. W.; Rothman, R. B.; Carroll, F. I. J. Chem. Soc., Chem. Commun. 1993, 758-760.
9. Akhrem, A. A.; Ukhova, L. I.; Uskova, N. F.; Prokofev, T. E. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 647-655; Khim. Geterotsikl. Soedin. 1977, 796-804.
10. Akhrem, A. A.; Ukhova, L. I.; Uskova, N. F.; Prokofev, T. E. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 647-655; Khim. Geterotsikl. Soedin. 1977, 796-804.
11. Courtin, J. M. L.; Verhagen, L.; Biesheuvel, P. L.; Lugtenburg, J.; van der Bend, R. L.; van Dam, K. Red. Trav. Chim. Pays-Bas 1987, 106, 112-119.
12. Harding, K. E.; Ligon, R. C. Synth. Commun. 1974, 4, 297-301.
13. Molloy, B. B.; Hauser, K. L. Chem. Commun. 1968, 1017-1019.
14. Korshevets, I. K.; Mistryukov, É. A. Bull Acad. Sci. USSR 1987, 1420-1425; Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 1540-1545.
15. Korshevets, I. K.; Mistryukov, É. A. Bull Acad. Sci. USSR 1987, 1420-1425; Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 1540-1545.
16. Long-range coupling in cyclohexanones is observed between both diequatorial and diaxial 2- and 6-protons, but not between equatorial and axial protons: Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon: Oxford, 1969; p 338.
17. Model, version KS 2.99 obtained from Kosta Steliou, Boston University, was used for MM2 calculations.
18. Mistryukov, E. A.; Smirnova, G. N. Tetrahedron 1971, 27, 375-377.
19. Chlorination of the nitrogen raises the barrier to inversion by ≈4 kcal/mol: (a) Anet, F. A. L.; Yavari, I. Tetrahedron Lett. 1977, 3207-3210. (b) Anet, F. A. L.; Yavari, I. J. Am. Chem. Soc. 1977, 99, 2794.
20. Chlorination of the nitrogen raises the barrier to inversion by ≈4 kcal/mol: (a) Anet, F. A. L.; Yavari, I. Tetrahedron Lett. 1977, 3207-3210. (b) Anet, F. A. L.; Yavari, I. J. Am. Chem. Soc. 1977, 99, 2794.
21. 13C NMR spectra of cylindricines A, B, and D.