Synthesis of the octahydroindole core of aeruginosins: A new bicyclic α-amino acid

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1899-1902

  Bonjoch, Josep ^a   Catena, Juanlo ^a   Isábal, Esther ^a   López Canet, Meritxell ^a   Valls, Nativitat ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AERUGINOSIN; AMINO ACID DERIVATIVE; ENZYME INHIBITOR; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0030200972     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00225-X     Document Type: Article

References (12)

1. 1. Murakami, M.; Okita, Y.; Matsuda, H.; Okino, T.; Yamaguchi, K. Tetrahedron Lett. 1994, 35, 3129.
2. 2. Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785.
3. 3. This work was presented in a preliminary form at the Eighth International Symposium on Marine Natural Products, Santa Cruz de Tenerife, Spain, September, 1995.
4. 4. Siedel, W.; Sturm, K.; Geiger, R. Chem. Ber. 1963, 96, 1436; Chem. Abstr. 1963, 59, 2951e.
5. 4. Siedel, W.; Sturm, K.; Geiger, R. Chem. Ber. 1963, 96, 1436; Chem. Abstr. 1963, 59, 2951e.
6. 5. The same reaction sequence has been communicated previously, but without any reference to the experimental procedure, nor to the yield of the process and strereochemical course of cyclization step: Sawlewicz, P.; Barska, I.; Smulkowski, M.; Gumieniak, J.; Czamomska, T.; Dzieduszycka, M.; Borowski, E. Rocz. Chem. 1976, 50, 1005.
7. 6. Enantiomeric purity of 5 and 6 was confirmed by registration of the nmr spectra of their salts with both enantiomers of Mosher's acid . For the procedure, see: Villani, Jr. F. J.; Costanzo, M. J.; Inners, R. R.; Mutter, M. S.; McClure, D. E. J. Org. Chem. 1986, 51, 3715.
8. 3: C, 76.01; H, 6.93; N, 3.85. Found: C, 76.02; H, 7.10; N, 3.83.
9. 1H nmr data (500 MHz) with those of racemic 10 of which the X-ray data are available: Souchet, M.; Guilhem, J.; Le Goffic, F. Tetrahedron Lett. 1987, 28, 2371.
10. 3) in the presence of 15 mg of (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol.
11. 4 241.1314, found 241.1320.
12. 11. For instance, treatment of β-amino ketone 7, exo compound, with MeOH-HCl(g) at reflux affords the corresponding methyl ester 8 of the endo series.