Hydroxynaphthyl C-glycosides via chromium-mediated benzannulation of a sugar alkyne

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 487-488

  Paetsch, Daphne ^a   Dötz, Karl Heinz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Benzannulation; Carbenes and carbenoids; Carbohydrates; Chromium carbenes; Glycosides

Indexed keywords

GLYCOSIDE;

ANTIBIOTIC THERAPY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; DRUG SYNTHESIS;

EID: 0033555240     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02488-5     Document Type: Article

References (12)

1. Organotransition Metal Modified Sugars, Part 12. For part 11, see: Dötz KH, Paetsch D, Le Bozec H, submitted for publication.
2. a) Hacksell U, Davies Jr. GD. Prog. Med. Chem. 1985;22: 1;
3. b) Suzuki K, Matsumoto T. Total synthesis of Aryl C-Glycoside antibiotics. In: Lukacs G, editor. Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, vol 2. Berlin: Springer-Verlag, 1993, 352.
4. Reviews: a) Postema MHD. Tetrahedron 1992;40:8545;
5. b) Jaramillo J, Knapp S. Synthesis 1994:1.
6. a) Dötz KH, Angew. Chem., Int. Ed. Engl. 1975; 14:644;
7. for reviews, see: b) Dötz KH, Angew. Chem., Int. Ed. Engl. 1984;23:587;
8. c) Wulff WD in Abel EW, Stone FGA, Wilkinson G, editors, Comprehensive Organometallic Chemistry II, vol. 12 Oxford, Pergamon Press, 1995, 469.
9. After this work was finished less reactive alkoxycarbene chromium complexes have been also used in benzannulation reactions with glucose and glucal derived ethynes. However, the harsher conditions required (THF, 55°C) did not allow for the isolation of metal-coordinated annulation products: Pulley SR, Carey JP. J. Org. Chem. 1998;63:5275.
10. Modified procedure according to Kraus GA, Molina MT. J. Org. Chem. 1988;53:742.
11. Fischer EO, Held W, Kreißl FR, Frank A, Huttner G. Chem. Ber. 1977; 110:656.
12. 3), 70.5 (C-6), 88.1 (C-1), 78.8, 78.8. 80.6, 85.0 (4 C, C-2-C-5) ppm.