Health & Environmental Research Online (HERO)


Print Feedback Export to File
7434910 
Journal Article 
STUDIES OF THE CYCLIC AMIDOACETAL CARBAMATE MOIETY OF THE MAYTANSINOIDS 
Gormley, G; Chan, YY; Fried, J 
1980 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
45 
8 
1447-1454 
English 
WOS:A1980JN37600021 
A synthesis of cyclic urethane amidoacetals of the type present in the maytansinoid ansa macrolides is reported both to serve as a synthetic model and to explore the chemistry of the hydroxylated intermediates of structures 5 and 6. These compounds are prepared by aldol cyclization of the open-chain amidoacetal aldehyde 4e. Compound 5 is the product of kinetic control, which rearranges to the stable isomeric end products 6 and 7, the latter of which possesses a five-membered urethane ring. The elucidation of structure, stereochemistry, and conformation of these substances is described. The removal of the secondary hydroxyl group of 5 to form 17a is accomplished in three steps. © 1980, American Chemical Society. All rights reserved. 
maytansine; drug structure; drug synthesis 
Other
• Harmful Algal Blooms- Health Effects
     April 2021 Literature Search
          WOS
          Scopus
          Saxitoxins
               WOS