Natural products analogs as Scaffolds for supramolecular and combinatorial chemistry

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5709-5712

  Mink, Daniel ^a   Mecozzi, Sandro ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amino acids and derivatives; Combinatorial Chemistry; Macrocycles; Oxazoles

Indexed keywords

DOLASTATIN; DOLASTATIN E; NATURAL PRODUCT; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032491014     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01170-8     Document Type: Article

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34. 18. Conditions for the macrocyclization: Linear trimer (0.151 mmol) in 10ml of anhydrous dimethylformammide was added to a stirred solution of O-(7-Azabenzotriazol-l-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.453 mmol) and 2,4,6 collidine (0.483 mmol) in 125ml of anhydrous dimethylformammide via syringe pump over a period of two days. Solvent was then evaporated in vacuo and the residue was taken up in 20ml of | N hydrochloric acid and 100ml of ethyl acetate. Aqueous layer was extracted two more times with with ethyl acetate (2×50ml) and the combined organic layers were washed with brine (2×10ml), dried with anhydrous magnesium sulfate and evaporated in vacuo. Pure 9a was obtained by column chromatography (chloroform/methanol 95:5).
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38. +: expected 460; found 460.