Asymmetric synthesis of 1-aminopentadecane-3,5,7,9,11,13,15-heptols and of 1,15-diaminopentadecane-3,5,7,9,11,13-hexols and derivatives

Synthesis

Volumn , Issue 14, 2002, Pages 1979-1986

  Gerber Lemaire, Sandrine ^a   Popowycz, Florence ^a   Glanzmann, Cécile ^a   Vogel, Pierre ^a  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

Author keywords

2,2 methylenedifuran; Aminopolyketide; Asymmetric synthesis; Diaminopolyketide; Long chain aminopolyols

Indexed keywords

DERIVATIVES; ORGANIC COMPOUNDS;

ENANTIOMERICALLY ENRICHED;

SYNTHESIS (CHEMICAL);

1 AMINOPENTADECANE 3,5,7,9,11,13,15 HEPTOL DERIVATIVE; 1,15 DIAMINOPENTADECANE 3,5,7,9,11,13 HEXOL DERIVATIVE; 15 AMINO 5,7,9,11 TETRAHYDROXY 3,13 BIS[(4 METHOXYBENZOYLOXY)PENTADEC 1 YL]PIVALATE; 2,2' METHYLENEDIFURAN; BENZOIC ACID DERIVATIVE; FURAN DERIVATIVE; HEPTANOL; INOSITOL DERIVATIVE; PIVALIC ACID; POLYKETIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0036400333     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34381     Document Type: Article

References (13)

1. Sakuda, S.; Guce-Bigol, U.; Itoh, M.; Nishimura, T.; Yamada, Y. J. Chem. Soc., Perkin Trans. 1 1996, 2315.
2. (a) Silo-Suh, L. A.; Stabb, E. V.; Raffel, S. J.; Handelsman, J. Curr. Microbiol. 1998, 37, 6.
3. (b) Stohl, E. A.; Milner, J. L.; Handelsman, J. Gene 1999, 237, 403.
4. (a) Harris, J. M. Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications; Harris, J. M., Ed.; Plenum Press: New York, 1992.
5. (b) Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1991, 56, 4326.
6. (c) Cook, R. M.; Adams, J. H.; Hudson, D. Tetrahedron Lett. 1994, 35, 6777.
7. (d) Schwabacher, A. W.; Lane, J. W.; Schiesher, M. W.; Leigh, K. M.; Johnson, C. W. J. Org. Chem. 1998, 63, 1727.
8. Schwenter, M. E.; Vogel, P. Chem.-Eur. J. 2000, 6, 4091.
9. Csákÿ, A. G.; Vogel, P. Tetrahedron: Asymmetry 2000, 11, 4935.
10. Schwenter, M. E.; Vogel, P. J. Org. Chem. 2001, 66, 7869.
11. (a) Nasaraka, K.; Pai, F. G. Tetrahedron Lett. 1984, 40, 2233.
12. Chen, K. N.; Hardtmann, G. E.; Prasad, K.; Repi, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
13. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.