Synthesis of Hydroazulene Derivatives via Iron Carbonyl-Promoted Cyclocarbonylation of 1,8-Diynes

Synlett

Volumn 1997, Issue 11, 1997, Pages 1281-1282

  Pearson, Anthony J ^a   Yao, Xin ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002800458     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1026     Document Type: Article

References (13)

1. (a) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202.
2. (b) Pearson, A. J.; Shively, R. J., Jr.; Dubbert, R. A.Organometallics 1992, 11, 4096.
3. (c) Pearson, A. J.; Shively, R. J., Jr. Organometallics 1994, 13, 578.
4. (d) Pearson, A. J.; Perosa, A. Organometallics 1995, 14, 5178.
5. (a) Knölker, H.-J.; Heber, J.; Mahler, C. H. Synlett 1992, 1002.
6. (b) Knölker, H.-J.; Heber, J. Synlett 1993, 924.
7. (c) For earlier studies on this cyclocarbonylation reaction, which gave lower yields than the protocol developed by our group and Knölker, see: Dickson, R. S.; Mok, C.; Connor, G. Aust. J. Chem. 1977, 30, 2143.
8. (a) Gesing, E. R. F.; Tane, J. P.; Vollhardt, K. P. C. Angew. Chem. Int. Ed. Engl. 1980, 19, 1023.
9. (b) Halterman, R. L.; Vollhardt, K. P. C. Organometallics 1988, 7, 883.
10. For a rather old, but still very useful overview of sesquiterpenoid synthesis, that includes a large number of hydroazulene systems, see: Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. Total Synthesis of Sesquiterpenes, 1970-79, in The Total Synthesis of Natural Products, Ed. ApSimon, J. Vol. 5, John Wiley & Sons, New York, 1983.
11. +) calcd 306.1471, found 306.1469.
12. 3Si) prevents this reaction, see reference 3 and: Allen, C. F. H.; VanAllan, J. A. J. Am. Chem. Soc. 1950, 72, 5165.
13. Shvo Y.; Hazum, E. J. Chem. Soc., Chem. Commun. 1974, 336.