A progressive synthetic strategy for class B synergimycins

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2147-2150

  Robinson, Jennifer L ^a   Taylor, Rachel E ^a   Liotta, Lisa A ^a   Bolla, Megan L ^a   Azevedo, Enrique V ^a   Medina, Irene ^a   McAlpine, Shelli R ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

Antibiotic; Class B; Synergimycin; Virginiamycin

Indexed keywords

ANTIBIOTIC AGENT; MACROCYCLIC COMPOUND; SYNERGIMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 1242272921     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.048     Document Type: Article

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20. Yield ranges reflect those for each individual amino acid monomer that is used in that particular step of the synthesis, that is, yields vary depending on the unique amino acid used in the reaction at that stage of the synthesis.
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22. Bolla M.L., Azevedo E.V., Smith J.M., Taylor R.E., Ranjit D.K., Segall A.M., McAlpine S.R. Org. Lett. 5:2003;109-112. Ring-closing reactions are slow and typically low yielding. Unpublished results from the Guy Laboratory at UCSF, and our laboratory have found that the use of several coupling reagents facilitates ring-closing reactions by providing a choice of reagents for the specific substrate. This is in lieu of optimizing each individual reaction for each individual coupling agent.
23. +], and +1 being those peaks):
24. The final macrocyclic class B derivative has the following data: (MW=901) MS: 946.5. 924.5, 924.4. Yield: 60% for two steps Purity: ~80%.
25. All compounds were characterized using NMR and LCMS.