A Methodology for Spirocyclopentannulation. Stereoselective Total Synthesis of (±)-Tochuinyl Acetate ana (±)-Dihydrotochuinyl Acetate

Synlett

Volumn 1996, Issue 1, 1996, Pages 67-68

  Srikrishna, A ^a   Reddy, T Jagadeeswar ^a   Kumar, P Praveen ^a   Vijaykumar, D ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003032765     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5318     Document Type: Article

References (17)

1. Ramaiah, M. Synthesis, 1984, 529; Paquette, L.A. Topics in Current Chemistry, 1984, 119, 1; Mehta, G; Karra, S.R. Tetrahedron Lett., 1991, 32, 3215 and references cited therein.
2. Ramaiah, M. Synthesis, 1984, 529; Paquette, L.A. Topics in Current Chemistry, 1984, 119, 1; Mehta, G; Karra, S.R. Tetrahedron Lett., 1991, 32, 3215 and references cited therein.
3. Ramaiah, M. Synthesis, 1984, 529; Paquette, L.A. Topics in Current Chemistry, 1984, 119, 1; Mehta, G; Karra, S.R. Tetrahedron Lett., 1991, 32, 3215 and references cited therein.
4. (a) Kuroda, C.; Hirono, Y. Tetrahedron Lett., 1994, 35, 6895;
5. (b) Pohmakotr, M.; Phinyocheep, P. Tetrahedron Lett., 1984, 25, 2249;
6. (c) Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y.; Akai, S.; Kita, Y. Tetrahedron Lett., 1995, 36, 3219 and references cited therein.
7. Srikrishna, A.; Sundarababu, G. Tetrahedron, 1990, 46, 3601.
8. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett., 1976, 2975.
9. (a) Okano, K.; Suemune, H.; Sakai, K. Chem. Pharm. Bull., 1988, 36, 1379;
10. (b) Karpf, M.; Drieding, A.S. Helv. Chim. Acta, 1979, 62, 852.
11. Reference 5a and references cited therein.
12. Williams, D.E.; Andersen, R.J. Can. J. Chem., 1987, 65, 2244.
13. There is no report on the total synthesis of dihydrotochuinyl acetate. For the synthesis of tochuinyl acetate see: (a) Taber, D.F.; Hennessy, M.J.; Louey, J.P. J. Org. Chem., 1992, 57, 436; (b) Nakatani, H.; So, T.S.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull., 1990, 38, 1233.
14. There is no report on the total synthesis of dihydrotochuinyl acetate. For the synthesis of tochuinyl acetate see: (a) Taber, D.F.; Hennessy, M.J.; Louey, J.P. J. Org. Chem., 1992, 57, 436; (b) Nakatani, H.; So, T.S.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull., 1990, 38, 1233.
15. +, 40%), 215 (30), 186 (80), 158 (70), 145 (90), 1311 (100), 119 (85).
16. 8a
17. 1H NMR spectrum of 13.