Synthesis of eight-membered ring compounds using enyne metathesis

Organic Letters

Volumn 2, Issue 4, 2000, Pages 543-545

  Mori, Miwako ^a   Kitamura, Tsuyoshi ^a   Sakakibara, Norikazu ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001603182     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991398a     Document Type: Article

References (20)

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2. (b) Furstner, A. Topics in Organometallic Chemistry; Vol 1, Springer-Verlag: Berlin Heidelberg, 1998; Vol 1.
3. (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 109, 737.
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5. (c) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049
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8. (f) Watanuki, S.; Ochifuji, N.; Mori, M. Organometallics 1994, 13, 4129.
9. (g) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
10. (h) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356.
11. (i) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073.
12. (j) Barrett, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. J. Chem. Soc., Chem. Commun. 1997, 1375.
13. (k) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287.
14. (l) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
15. (m) Kinoshita, A.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
16. The reaction course for intramolecular enyne metathesis is as shown: (formula presented) Methylidene ruthenium-carbene complex i, which is formed from benzylidene carbene complex, reacts with alkyne to form ruthenacyclobutene ii via [2 + 2] cycloaddition. It is then converted into vinylcarbene complex iii, which reacts with olefin in a tether to give ruthenacyclobutane iv. and then bond fission occurs to give cyclized diene 3 and methylidene ruthenium complex i. Thus, the catalytic cycle is established. When i reacts first with the olefin moiety of enyne 2, a similar catalytic cycle would occur. Compare with ref 2a and Hoye, R. T.; Donaldoson, S. M.; Vos, T. Org. Lett. 1999, 1, 276.
17. Synthesis of eight-membered ring compounds using olefin metathesis was reported: Miller, S. J.; Kim, S.-H.; Chen, Z.-R. Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108.
18. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
19. In the synthesis of an eight-membered ring compound from 4 using enyne metathesis, many pathways, such as the formation of the eight-membered ring compound 5 or nine-membered ring compound 17, or a medium-sized ring compound having cis-or trans-olefin, were considered: (formula presented) However, it is difficult to distinguish which compound is formed in this reaction from the spectral data. Thus, the structure of 5d was determined by X-ray crystallography, and it is confirmed that an eight-membered ring compound was formed in this reaction.
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