De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6686-6689

  Ahmed, Md Moinuddin ^a   Cui, Hu ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIENOATES; DIHYDROXYLATION; ENANTIOMERS; MURICATACIN; STEREOSELECTIVE SYNTHESIS;

CHEMICAL REACTIONS; DERIVATIVES; ORGANIC CHEMICALS; SYNTHESIS (CHEMICAL);

ESTERS;

GAMMA BUTYROLACTONE DERIVATIVE; MURICATACIN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DIHYDROXYLATION; ENANTIOMER; ENANTIOSELECTIVITY; EPIMER; REACTION ANALYSIS;

FURANS; HYDROXYLATION; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33747410110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061057s     Document Type: Article

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33. All enantiomeric excesses were determined by chiral HPLC (for details see Supporting Information).
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35. Presented in this text are the experimental procedures for the preparation of compounds 9-12. Complete experimental procedures and spectral data for all compounds are presented in the Supporting Information.
36. While we were able to generate a molecular ion for dienoate 6 using electron impact ionization, we were unable to generate a molecular ion using electrospray ionization techniques, thus we were unable to obtain any high-resolution mass data.
37. High-resolution MS data was not obtained for the enantiomers of compounds 4 and 5.