Benzothiazines in synthesis. A formal total synthesis of pseudopteroxazole

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5559-5561

  Harmata, Michael ^a   Cai, Zhengxin ^a   Chen, Yugang ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; ESTER GROUPS; METHYL GROUP; NATURAL PRODUCTS; TOTAL SYNTHESIS;

ESTERS; HYDROCARBONS;

SYNTHESIS (CHEMICAL);

BENZOTHIAZINE DERIVATIVE; PSEUDOPTEROXAZOLE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; STEREOCHEMISTRY;

ANTITUBERCULAR AGENTS; BIOLOGICAL FACTORS; CYCLIZATION; DITERPENES; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM; THIAZINES;

EID: 68049095154     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9009112     Document Type: Article

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19. Only trace amounts of a compound assigned as an intramolecular Heck reaction product were isolated whenever this reaction was performed. This product 16 was characterized and details on it are reported in the Supporting Information. The enantiopurity of 12 is considered to be the same as that of (R)-11, which was established by both optical rotation and HPLC to be 100%, within experimental error.
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21. Diastereomeric ratios were determined based on proton NMR analysis of crude reaction mixtures. The diastereoselectivity varied from 7 to 10:1. The minor isomer was not characterized but could be separated from the desired diastereomer by column chromatography.