Elaboration of S-(-)-α-Pinene into Functionalized Bicyclo[4.2.1]nonane Framework of Mediterraneols

Synlett

Volumn 1997, Issue 10, 1997, Pages 1161-1162

  Mehta, Goverdhan ^a   Acharyulu, P V R ^a   Reddy, K Subba ^a   Umarye, Jayant D ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002518134     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-985     Document Type: Article

References (13)

1. (a) Wender, P.A.; Wessjohann, L.A.; Peschke, B.; Rawlins, D.B. Tetrahedron Lett. 1995, 36, 718 and earlier references.
2. (b) Winkler, J.D.; Bhattacharya, S.K.; Liotta, F.; Batey, R.A.; Heffenan, G.D.; Cladingboel, D.E.; Kelly, R.C. Tetrahedron Lett. 1995, 36, 2211.
3. (a) Francisco, C.; Banaigs, B.; Teste, A.; Cave, A. J. Org. Chem. 1986, 51, 1115.
4. (b) Kakiuchi, K.; Nakamura, I.; Matsuo, F.; Nakota, M.; Ogura, M.; Tobe, Y.; Kurosawa, H. J. Org. Chem. 1995, 60, 3318. These authors have synthesized tetramethylmediterraneol B, a derivative of 2 and concluded that structure of 2 needs revision. However, the correction does not influence the basic carbocyclic skeleton present in the natural product 2.
5. Hadjiarapoglan, L.; Klein, I.; Spitzner, D.; de Meijere, A.; Synthesis 1996, 525; Kakiuchi, K.; Fukunaga, K.; Matsuo, F.; Ohnishi, Y.; Tobe, Y. J. Org. Chem. 1991, 56, 6742 and earlier references cited in these papers.
6. Hadjiarapoglan, L.; Klein, I.; Spitzner, D.; de Meijere, A.; Synthesis 1996, 525; Kakiuchi, K.; Fukunaga, K.; Matsuo, F.; Ohnishi, Y.; Tobe, Y. J. Org. Chem. 1991, 56, 6742 and earlier references cited in these papers.
7. Mehta, G.; Rao, H.S.P. Syn. Commun. 1985, 15, 991.
8. Bak, D.A.; Brady, W.T. J. Org. Chem. 1979, 44, 107. These authors report 16% yield in the addition of dichloroketene to α-pinene.
9. Fletcher, V.R.; Hassner, A. Tetrahedron Lett. 1970, 1071.
10. (a) Mehta, G.; Acharyulu, P.V.R. Tetrahedron Lett. 1993, 34, 8157.
11. (b) Mehta, G.; Acharyulu, P.V.R. J. Chem. Soc. Chem. Commun., 1994, 37, 2655.
12. +).
13. Barthelemy, M.; Gianfermi, A.; Bessiere, Y. Helv. Chim. Acta 1976, 59, 193.