Stereoselective routes to densely functionalized cis-hydrindanes: Synthetic intermediates for reserpine

Synlett

Volumn , Issue 5, 1997, Pages 612-614

  Mehta, Goverdhan ^a   Reddy, D Srinivasa ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748657909     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3218     Document Type: Article

References (17)

1. For the total synthesis of reserpine accomplished so far, see: (a) Woodward, R.B.; Bader. F.E.; Bickel, H.; Frey, A.J.; Kierstead, R.W. J. Am. Chem. Soc. 1956, 78, 2023.
2. (b) Pearlmann, B.A. J. Am. Chem. Soc. 1979, 101, 6404.
3. (c) Wender, P.A.; Schaus, J.M.; White, A.W. J. Am. Chem. Soc. 1980, 102, 6159.
4. (d) Martin, S.F.; Grzejszczak, S.; Rueger, H.; Williamson, S.A. J. Am. Chem. Soc. 1987, 109, 6124.
5. (e) Stork, G. Pure & Appl. Chem. 1989, 61, 439.
6. (f) Gomez, A.M.; Lopez, J.C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3859.
7. (g) Chu, C-S.; Liao, C-C; Rao, P.D. J. Chem. Soc. Chem. Commun. 1996, 1537.
8. cis-Hydrindane-based approaches to reserpine have been explored, but all these are conceptually different from the one described here. See: (a) Jung, M.E.; Light, L.A. J. Am. Chem. Soc. 1984, 106, 7614.
9. (b) Polniaszek, R.P.; Stevens, R.V. J. Org. Chem. 1986, 51, 3023.
10. (c) Toyota, M.; Matuura, M.; Fukumoto, K. Heterocycles, 1995, 41, 661.
11. (d) Toyota, M.; Wada, T.; Matsuura, M.; Fukumoto, K. Synlett, 1995, 761.
12. Schuda, P.F.; Ammon, H.L.; Heimann, M.R.; Bhattacharjee, S. J. Org. Chem. 1982, 47, 3434.
13. (a) Mehta, G.; Praveen, M. J. Chem. Soc. Chem. Commun. 1993, 1573.
14. (b) Hamlin, K.E.; Weston, A.W. Org. React., 1957, 9, 1.
15. (c) Paquette, L.A.; Maynard, G.D. J. Org. Chem., 1989, 54, 5054 and earlier related papers of mechanistic interest.
16. 3): δ 173.0, 171.9, 118.1, 74.5, 72.9, 65.0, 63.9, 51.6, 48.8, 40.8, 38.9, 32.9, 30.1, 21.1, 20.4.
17. 4 requires C: 65.53; H, 7.61%).