Diastereoselective elaboration of 2,3,4-substituted piperidines using diene iron tricarbonyl complexes. Total synthesis of (±)-dienomycin C and (±)-4-epi-dienomycin C

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3991-3992

  Ripoche, Isabelle ^a   Bennis, Khalil ^a   Canet, Jean Louis ^a   Gelas, Jacques ^a   Troin, Yves ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DIENOMYCIN C; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029973851     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00621-1     Document Type: Article

References (11)

1. Ripoche, I.; Gelas, J.; Grée, D.; Grée, R.; Troin, Y.; Tetrahedron Lett. 1995, 36, 6675-6678.
2. a) Umezawa, S.; Tsuchiya, T.; Tatsuta, K.; Horiuchi, Y.; Usui, T.; Umezawa, H.; Hamada, M.; Yagi, A. J. Antibiot. 1970, 23, 20-27;
3. b) Umezawa, S.; Tatsuta, K.; Horiuchi, Y.; Tsuchiya, T.; Umezawa, H.; J. Antibiot. 1970, 23, 28-34.
4. 5 (85% yield).
5. Bosch, J.; Rubiralta, M.; Moral, M.; Valls, M.; J. Heterocyclic Chem., 1983, 20, 595-605.
6. Clinton, N.A.; Lillya, C.P.; J. Am. Chem. Soc., 1970, 92, 3058-3064.
7. All new compounds were identified by their spectral and analytical data.
8. Stephenson, G.R.; Finch, H.; Owen, D.A.; Swanson, S.; Tetrahedron, 1993, 49, 5649-5662.
9. Equilibration to the more stable compound is observed.
10. This reagent is known to give an equatorial attack on hindered cyclanones : Seyden-Penne, J.; "Réductions par les alumino et borohydrures en synthèse organique"; Lavoisier, Paris, 1988.
11. 1H NMR spectroscopy.