Synthesis of the bicyclo[4.3.1]decenone core of CP-225,917 and CP-263,114

Synlett

Volumn , Issue 5, 1998, Pages 552-553

  Armstrong, Alan ^a   Critchley, Trevor J ^a   Mortlock, Andrew A ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002710195     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1699     Document Type: Article

References (16)

1. Dabrah, T.T.; Kaneko, T.; Massefski Jr., T.; Whipple, E.B. J. Am. Chem. Soc. 1997, 119, 1594-1598.
2. Dabrah, T.T.; Harwood Jr., H.J.; Huang, L.H.; Jankovich, N.D.; Kaneko, T.; Li, J-C.; Lindsey, S.; Moshier, P.M.; Subashi, T.A.; Therrien, M.; Watts, P.C. J. Antibiot. 1997, 50, 1-7.
3. For a review of ras-farnesyl protein transferase inhibition, see: Buss, J.E.; Morsters, J.C. Chem. Biol. 1995, 2, 787-791.
4. Barton, D.H.R.; Sutherland, J.K.; J. Chem. Soc. 1965, 1769-1772, and subsequent papers.
5. Davies, H.M.L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740.
6. Nicolaou, K.C.; Härter, M.W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196.
7. Nicolaou, K.C.; Postema, M.H.D.; Miller, N.D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823.
8. Sgarbi, P.W.M.; Clive, D.L.J. Chem. Commun. 1997, 2157-2158.
9. Procopiou, P.A.; Baugh, S.P.D.; Flack, S.S.; Inglis, G.G.A. Chem. Commun. 1996, 2625-2626.
10. 5 requires 254.1154.
11. A similar Mukaiyama aldol reaction has been used to make the corresponding saturated ring system, bicyclo[4.3.1]decanone: Kellner, D.; Loewenthal, H.J.E. Tetrahedron Lett. 1983, 24, 3397-3400.
12. Mukaiyama, T. Org. React. 1982, 28, 203-331.
13. 6 requires 325.1651.
14. -1) for bicyclo[4.3.1]dec-1-en-10-one itself: Cordiner, B.C.; Vegar, M.R.; Wells, R. Tetrahedron Lett. 1970, 2285-2286.
15. Compound Sb displayed an NOE to H11 on irradiation of H10; this interaction was not evident in the NOESY spectrum of 5a. MM2 * calculations in MacroModel 5.5 (Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440-467) suggest that an NOE between H10 and H11 is unlikely in the preferred conformations of the compound with stereochemistry 5a, whereas the H10-H11 distance is relatively short in 5b.
16. Fletcher, D.A.; McMeeking, R.F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.