Total Synthesis and Structure of the Ramoplanin A1 and A3 Aglycons: Two Minor Components of the Ramoplanin Complex

Ramoplanin is a potent antibiotic, first disclosed in 1984, that acts by inhibiting bacterial cell-wall biosynthesis. The original ramoplanin complex was shown to consist of a mixture of three closely related compounds, ramoplanin A1-A3, of which ramoplanin A2 is the most abundant. The structure of...

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Published inProceedings of the National Academy of Sciences - PNAS Vol. 101; no. 33; pp. 11977 - 11979
Main Authors Shin, Dongwoo, Rew, Yosup, Boger, Dale L., Nicolaou, Kyriacos C.
Format Journal Article
LanguageEnglish
Published United States National Academy of Sciences 17.08.2004
National Acad Sciences
SeriesNatural Product Synthesis Special Feature
Subjects
Anhydrides
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Antibiotics
Bacteria
Carboxylic acids
Cells
Chemical synthesis
Chemistry
Chemistry, Organic - methods
Depsipeptides
Lipids
Molecular Structure
Natural Product Synthesis Special Feature
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Physical Sciences
Stereochemistry
Stereoisomerism
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Summary:Ramoplanin is a potent antibiotic, first disclosed in 1984, that acts by inhibiting bacterial cell-wall biosynthesis. The original ramoplanin complex was shown to consist of a mixture of three closely related compounds, ramoplanin A1-A3, of which ramoplanin A2 is the most abundant. The structure of ramoplanin A2 was unambiguously established first through a series of extensive spectroscopic studies, allowing complete stereochemical assignments and subsequently providing a minor reassignment of the side-chain double-bond stereochemistry and, most recently, through total synthesis of authentic material. Here we report the total syntheses of the aglycons of the minor components of the ramoplanin complex, A1 and A3, which unambiguously establish their structure and provide an expected structural revision for the lipid side-chain double-bond stereochemistry.
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Edited by Kyriacos C. Nicolaou, The Scripps Research Institute, La Jolla, CA
To whom correspondence should be addressed. E-mail: boger@scripps.edu.
This paper was submitted directly (Track II) to the PNAS office.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0401419101