Cobalt-mediated cyclization of amino acid derivatives. Application to the kainoids

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 3, 1987, Pages 166-168

  Baldwin, Jack E ^a   Li, Chun Sing ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049087280     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39870000166     Document Type: Article

References (19)

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2. J. M. Pratt and P. J. Craig, Adv. Organomet. Chem., 1973, 11, 331.
3. D. Dodd and M. D. Johnson, J. Organomet. Chem., 1973, 52, 1.
4. For recent synthesis of kainoids: kainic acid: W. Oppolzer and K. Thirring, J. Am. Chem. Soc., 1982, 104, 4978.
5. Allokainic acid: P. De Shong and D. A. Kell, Tetrahedron Lett., 1986, 27, 3979.
6. Domoic acid: Y. Ohfune and M. Tomita, J. Am. Chem. Soc., 1982, 104, 3511.
7. Acromelic acid A: K. Konno, K. Hashimoto, and Y. Ohfune, Tetrahedron Lett., 1986, 27, 607.
8. Acromelic acid B: K. Hashimoto, K. Konno, H. Shirahama, and T. Matsumoto, Chem. Lett., 1986, 1399.
9. For other applications of organocobalt chemistry in organic synthesis: review: R. Scheffold, G. Rytz, and L. Walder in ‘Modern Synthetic Methods,’ ed. R. Scheffold, 1983, vol. 3, pp. 355-440.
10. Functionalized butyrolactones: H. Bhandal, G. Pattenden, and J. J. Russell, Tetrahedron Lett., 1986, 27, 2299.
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12. M. Okabe, M. Abe, and M. Tada, J. Org. Chem., 1982, 47, 1775.
13. Heterocycles: V. F. Patel, G. Pattenden, and J. J. Russell, Tetrahedron Lett., 1986, 27, 2303.
14. Cobaloxime(i) was prepared in situ: G. N. Schrauzer, Inorg. Synth., 1968, 11, 61 or by sodium borohydride reduction of chlorocobaloxime(III).
15. Functionalized butyrolactones: H. Bhandal, G. Pattenden, and J. J. Russell, Tetrahedron Lett., 1986, 27, 2299.
16. For stereochemical studies of intramolecular radical cyclization reactions: K. N. Houk, M. N. Paddon-Row, N. G. Rondan, Y.-D. Wu, F. K. Brown, D. C. Spellmeyer, J. T. Metz, Y. Li, and R. J. Loncharich, Science, 1986, 231, 1108.
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19. W. R. Roush and M. A. Adam, J. Org. Chem., 1985, 50, 3752.