A new route to cumulenes by stannylation-deoxystannylation of propargylic alcohols. Application to synthesis of conjugated enyne[3]cumulene as a model compound of neocarzinostatin chromophore

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5549-5552

  Araki, Yoshitaka ^a   Konoike, Toshiro ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

Cumulenes; Elimination reactions; Silicon and compounds; Tin and compounds

Indexed keywords

ALCOHOL; CUMULENE; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG; ZINOSTATIN;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032581515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01117-4     Document Type: Article

References (18)

1. [1] Kawase, T.; Muro, S.: Kurata, H.; Oda, M. J. Chem. Soc., Chem. Commun. 1992, 778-779.
2. [2] Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68-76.
3. [3] Myers, A. G.: Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146-1147.
4. |4] For a review of related compounds, see: Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
5. [5] Hopf, H. In The Chemistry of Ketenes, Allenes, and Related Compounds, Part 2; Patai, S. Ed.; Wiley & Sons: New York, 1980; pp 863-881.
6. [6] Wang, K. K.; Liu, B.; Lu, Y. -D. Tetrahedron Lett. 1995, 36, 3785-3788.
7. [7] Scheuplein, S.: Machinek, R.; Suffert, J.; Brückner, R. Tetrahedron Lett. 1993, 34, 6549-6552.
8. [8] Fujiwara, K.; Sakai, H.; Hirama, M. J. Org. Chem. 1991, 56, 1688-1689.
9. (9] Saito, I.; Yamaguchi, K.; Nagata, R.; Murahashi, E. Tetrahedron Lett. 1990, 31, 7469-7472.
10. [10] Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093-5096.
11. [11] Solladié, G.; Adamy, M.; Colobert, F. J. Org. Chem. 1996, 61, 4369-4373.
12. [12] Copéret, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 3422-3431.
13. [13] Paquette, L. A.: Johnson, B. A.: Hinga, F. M. Organic Syntheses; Wiley & Sons: New York, 1973; Collect. Vol. V., pp 215-217.
14. [14] Sonogashira, K.: Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
15. [15] Chlorotrimethylstannane was used as a stannylating reagent for simplifying the NMR spectra of the intermediates and for comparing the reaction of the trimethylsilyl counterpart as described in the following section.
16. [16[ Chow, H. -F.; Cao, X. -P.: Leung, M. -K. J. Chem. Soc., Perkin Trans. 1 1995, 193-196.
17. [17] Chan, T. H.; Mychajlowskij, W.; Ong, B. S.; Harpp, D. N. J. Org. Chem. 1978, 43, 1526-1532.
18. [18] Omae, I. In Organotin Chemistry; Journal of Organometallic Chemistry Library 21; Elsevier Science: New York, 1989; p 19.