Total synthesis of (+)-apiosporamide: Assignment of relative and absolute configuration

Angewandte Chemie - International Edition

Volumn 44, Issue 41, 2005, Pages 6715-6718

  Williams, David R ^a   Kammler, David C ^a   Donnell, Andrew F ^a   Goundry, William R F ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Antifungal agents; Antitumor agents; Heterocycles; Lactams; Total synthesis

Indexed keywords

ACTIVATION ANALYSIS; AMINES; FUNGI; METABOLISM; TUMORS;

ANTIFUNGAL AGENTS; ANTIPODAL; ANTITUMOR AGENTS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

APIOSPORAMIDE; CYCLOHEXANOL DERIVATIVE; NAPHTHALENE DERIVATIVE; PYRIDONE DERIVATIVE; YM 215343; YM-215343;

ARTICLE; CHEMISTRY; CONFORMATION; OPTICAL ROTATION; STEREOISOMERISM; SYNTHESIS;

CYCLOHEXANOLS; MOLECULAR CONFORMATION; NAPHTHALENES; OPTICAL ROTATION; PYRIDONES; STEREOISOMERISM;

EID: 27444433686     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502015     Document Type: Article

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33. + 430.2224; found: 430.2225.
34. 13C NMR spectroscopic data, and the discrepancy in the specific optical rotation in 1, the route was adapted for independent preparation of three diastereomers with the syn relationship between the epoxide and tertiary alcohol (as in 8 and 9). All of these isomers demonstrated great instability and underwent opening of the oxirane, as illustrated in the formation of 24 through directed oxidation of 23. Interestingly, five-membered-ring products were not observed. Additional information will be provided in a full account. (Chemical Equation Presented)
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36. 24 = + 47° (c = 0.225 MeOH). Diastereoisomer 25 proved to be stable and spectroscopically similar to apiosporamide. However, oxidation gave ketone 26 which was clearly diastereomeric to 2. (Chemical Equation Presented)