Studies on the total synthesis of tallysomycin. Synthesis of the threonylbithiazole moiety containing a structurally unique glycosylcarbinolamide

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2811-2814

  Sznaidman, Marcos L ^a   Hecht, Sidney M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BLEOMYCIN; DRUG DERIVATIVE; TALLYSOMYCIN; THIAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BLEOMYCIN; THIAZOLES;

EID: 0035818027     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0101178     Document Type: Article

References (32)

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13. 2 in two ways, namely, the absence of a methyl group in the valerate moiety and the presence of two hydroxyl groups of undefined stereochemistry within the aminoethylbithiazole moiety, one of which is conjugated to a talose sugar as part of a glycosylcarbinolamide.
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19. (S)-Threonine was N-protected by treatment with a basic, aqueous solution of methyl chloroformate (Seebach, D.; Charczuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401), followed by silylation in an overall yield of 41%.
20. (R)-2,2-Dimethyl-1,3-dioxolane-4-carboxamide (Iwadare, K. Bull. Chem. Soc. Jpn. 1939, 14, 131) was converted to benzyl imidate 7 essentially quantitatively by treatment with benzyl iodide-silver oxide (Pougny, J.-R.; Sinaÿ, P. Tetrahedron Lett. 1976, 4073). The product contained ∼15% of the N-benzylamide and was used in the next step without further purification.
21. (R)-2,2-Dimethyl-1,3-dioxolane-4-carboxamide (Iwadare, K. Bull. Chem. Soc. Jpn. 1939, 14, 131) was converted to benzyl imidate 7 essentially quantitatively by treatment with benzyl iodide-silver oxide (Pougny, J.-R.; Sinaÿ, P. Tetrahedron Lett. 1976, 4073). The product contained ∼15% of the N-benzylamide and was used in the next step without further purification.
22. 1H NMR indicated that a single isomer, presently of unknown absolute configuration at the newly formed stereocenter, had been separated from the mixture of isomers formed during the reduction.
23. 14,15 Treatment with hydroxylamine hydrochloride then afforded 12 as colorless crystals in 50% overall yield from rhamnose.
24. 14,15 Treatment with hydroxylamine hydrochloride then afforded 12 as colorless crystals in 50% overall yield from rhamnose.
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31. 2S to afford the thioamide.
32. Thiazole 22 was obtained in six steps in 42% overall yield trom benzoyl chloride, acetaldehyde, sodium cyanide and ethyl bromopyruvate by minor modification of a published procedure (Sakai, T. T.; Riordan, J. M.; Booth, T. E.; Glickson, J. D. J. Med. Chem. 1981, 24, 279).