A concise entry into the bicyclo[6.4.0]dodecane system present in taxanes. Regioseleetive Haller-Bauer cleavage in tricyclo[8.2.1.02,9]tridecan-13-ones

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2289-2292

  Mehta, Goverdhan ^a   Reddy, K Subba ^a   Kunwar, Ajit C ^b  

^a UNIVERSITY OF HYDERABAD   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029974523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00245-6     Document Type: Article

References (8)

1. (a) Boa, A.N.; Jenkins, P.R.; Lawrence, N.J. Contemporary Organic Synthesis, 1994, 47.
2. (b) Petasis, N.A.; Patane, M.A. Tetrahedron, 1992, 48, 5757.
3. For use of 2 in synthesis see: (a) Mehta, G.; Rao, K.S.; J. Am. Chem. Soc., 1986, 108, 8015.
4. (b) Friedrich, D.; Paquette, L.A. J. Chem. Soc. Perkin Trans. 1, 1991, 1621.
5. For recent examples of the use of Haller-Bauer cleavage in natural product synthesis see: (a) Mehta, G.; Praveen, M. J. Chem. Soc. Chem. Commun, 1993, 1573. Mehta, G.; Praveen, M. J. Org. Chem, 1995, 60, 279 and references cited therein.
6. For recent examples of the use of Haller-Bauer cleavage in natural product synthesis see: (a) Mehta, G.; Praveen, M. J. Chem. Soc. Chem. Commun, 1993, 1573. Mehta, G.; Praveen, M. J. Org. Chem, 1995, 60, 279 and references cited therein.
7. Gassman, P.G.; Lumb, J.T.; Zalar, F.V. J. Am. Chem. Soc., 1967, 89, 946.
8. 3): δ 160.49, 139.96, 137.5, 136.70, 123.63, 51.4, 45.33, 39.81, 30.98, 30.49, 30.37, 25.10, 24.73, 24.24(2C), 24.11.