Synthesis of the optically active key intermediate of FR901483

Tetrahedron Letters

Volumn 51, Issue 31, 2010, Pages 4027-4029

  Ieda, Shigeru ^a   Kan, Toshiyuki ^b   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FR 901483; IMMUNOSUPPRESSIVE AGENT; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DIECKMANN REACTION; DRUG SYNTHESIS; POLYMERIZATION; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 77953962283     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.089     Document Type: Article

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34. Presumably, this reaction proceeds via oxazolonium intermediate 22 through neighboring group participation. As shown in Scheme 5, the acetamide moiety plays a key role in this transformation. This speculation is supported by the fact that the amide of the Passerini compound, which has an acetate instead of the acetamide moiety, was unaffected under the same methanolysis conditions. Trimethyl orthoformate played an important role for dehydration as well as trapping p-anisidine.
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37. 3b although it exclusively gave the 'undesired' stereoisomer for their synthetic studies
38. Similar stereochemistry of the aldol product was observed with 4a. Both hydroxy groups of 3a and 3b are equatorially oriented and syn to the carbonyl groups.
39. 3e