Chemistry and biology of diazonamide A: Second total synthesis and biological investigations

Journal of the American Chemical Society

Volumn 126, Issue 40, 2004, Pages 12897-12906

  Nicolaou, K C ^b   Hao, Junliang ^b   Reddy, Mali V ^b   Rao, Paraselli Bheema ^b   Rassias, Gerasimos ^b   Snyder, Scott A ^b   Huang, Xianhai ^b   Chen, David Y K ^b   Brenzovich, William E ^b   Giuseppone, Nicolas ^b   Giannakakou, Paraskevi ^b   O'Brate, Aurora ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; DEHYDRATION; SYNTHESIS (CHEMICAL);

CYCLODEHYDRATION; DIAZONAMIDES; SYNTHETIC ROUTES;

AMINES;

AMIDE; DIAZONAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 5644290625     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja040093a     Document Type: Article

References (46)

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29. This protocol represents a new method for MOM-cleavage on indoles, particularly for acid sensitive substrates since typical deprotection procedures utilize HCl at elevated temperatures. Since previous reports have already established the acid sensitivity of the aryl chlorines on the diazonamide skeleton bearing a free indole (see Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765-4770), the ability to initially cleave the methyl ether only, followed by basic hydrolysis, is crucial for the survival of the chlorines.
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32. Cells were plated in 96-well plates and incubated with either the test substrate or Taxol (as a positive control) for 72 h. The cells were then fixed and processed for growth inhibition using the sulforhodamine-B assay.
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40. One potential reason for the decreased yield of furan products could be a high enol content within the starting materials employed.
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