Stereoselective synthesis of substituted piperidines - Total synthesis and absolute configurations of (+)- and (-)-dienomycin C

European Journal of Organic Chemistry

Volumn , Issue 7, 1999, Pages 1517-1521

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

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Asymmetric synthesis; Chiral resolution; Natural prioducts; Piperidines; Tricarbonyliron complexes

Indexed keywords

DIENOMYCIN C; IRON COMPLEX; MANDELIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; DIASTEREOISOMER; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY; STREPTOMYCES;

EID: 0032775247     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199907)1999:7<1517::AID-EJOC1517>3.0.CO;2-H     Document Type: Article

References (17)

1. For a recent review on enantioselective synthesis of piperidine alkaloids, see: P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633-640.
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5. Preliminary report of part of this work: I. Ripoche, K. Bennis, J.-L. Canet, J. Gelas, Y. Troin, Tetrahedron Lett. 1996, 37, 3991-3992. Unfortunately, the described acidic oxo deprotection conditions could not be used, since partial epimerisation was observed.
6. [6a] S. Umezawa, T. Tsuchiya, K. Tatsuta, Y. Horiuchi, T. Usui, H. Umezawa, M. Hamada, A. Yagi, J. Antibiot. 1970, 23, 20-27.
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10. Enantiomeric excess determination was achieved by deuterium NMR in a liquid crystal: J.-L. Canet, I. Canet, J. Gelas, I. Ripoche, Y. Troin, Tetrahedron: Asymmetry 1997, 8, 2447-2451.
11. The amine 5 is conveniently prepared according to: J. Bosch, M. Rubiralta, M. Moral, M. Vails, J. Heterocycl. Chem. 1983, 595-605.
12. The ψ endo and ψ exo nomenclature was introduced by: N.A. Clinton, C.P. Lillya, J. Am. Chem. Soc. 1970, 92, 3058-3064.
13. [4]
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15. J. Seyden-Penne, Reductions by the Alumino and Borohydrides in Organic Synthesis, Wiley-VCH, New York, 1997 and references cited therein.
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17. We have recently reported a complete study on the enantiomeric separation of dienomycin C by chiral capillary electrophoresis: P. Morin, D. Bellesort, M. Dreux, Y. Troin, J. Gelas, J. Chromatogr. A 1998, 796, 375-383. Chiral capillary electrophoresis of synthetic (+)-1 and (-)-1, realised under the same conditions, gave in both cases only one peak.