Total Synthesis of Mycocyclosin

The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an int...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (9), p.2402-2405
Main Authors: Cochrane, James R, White, Jonathan M, Wille, Uta, Hutton, Craig A
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Diketopiperazines - chemical synthesis
Diketopiperazines - chemistry
Molecular Structure
Mycobacterium tuberculosis - chemistry
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Summary:The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura–Suzuki cross-coupling to generate the biaryl linkage.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300831t