Synthesis of barettin

Tetrahedron

Volumn 60, Issue 4, 2004, Pages 961-965

  Johnson, Ann Louise ^a,b   Bergman, Jan ^a,b   Sjögren, Martin ^c   Bohlin, Lars ^c  

^a KAROLINSKA INSTITUTE   (Sweden)

^b SÖDERTÖRN UNIVERSITY   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

Barettin; Geodia Barretti; HWE reaction; N Boc protection of arginine

Indexed keywords

6 BROMOINDOLE 3 CARBOXALDEHYDE; ALDEHYDE DERIVATIVE; ALKALOID DERIVATIVE; BARETTIN; INDOLE DERIVATIVE; PIPERAZINEDIONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; GEODIA BARRETTI; HORNER WADSWORTH EMMONS REACTION; PRIORITY JOURNAL; SPONGE (PORIFERA);

GEODIA;

EID: 0347600586     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.031     Document Type: Article

References (15)

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4. The formally correct name for 6-bromo-Δ-tryptophan is 2-amino-3-(6-bromo-1H-indol-3-yl)-acrylic acid.
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7. Cyclisation of the dipeptide ester was carried out by the acetic acid-catalysed method, see: Suzuki K., Sasaki Y., Endo N., Mihara Y. Chem. Pharm. Bull. 29:1981;233.
8. Sjögren, M.; Göransson, U.; Johnson, A.-L.; Dahlström, M. ; Andersson, R.; Bergman, J.; Jonsson, P. R.; Bohlin, L. J. Nat. Prod. In press.
9. 6-Bromo-Δ-tryptophan ethyl ester was prepared via stannous chloride reduction of 3-(6-bromo-1H-indol-3-yl)-2-nitro-acrylic acid ethyl ester. For analogous reactions, see: Aboskalova N.I., Babievskii K.K., Belikov V.M., Perekalin V.V., Ploanskaya A.S. J. Org. Chem. USSR (Engl. Transl.). 9:1973;1082.
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11. Schmidt U., Lieberknecht A., Wild J. Synthesis. 1984;53.
12. Via N-protection of 6-bromo-1H-indolyl-3-carboxaldehyde: Da Settimo A., Saettone M.F., Nannipieri P., Barili P. Gazz. Chim. Ital. 97:1967;1304.
13. Schmidt U., Griesser H., Leitenberger V., Lieberknecht A., Mangold R., Meyer R., Riedl B. Synthesis. 1992;487.
14. 13C NMR spectrum resonates at 124.5 ppm.
15. Kamlet M. J. Org. Chem. 24:1959;714.