Evaluation of the Biosynthetic Proposal for the Synthesis of Marineosins A and B
2010; American Chemical Society; Volume: 12; Issue: 5 Linguagem: Inglês
10.1021/ol100034p
ISSN1523-7060
AutoresLeslie N. Aldrich, Eric S. Dawson, Craig W. Lindsley,
Tópico(s)Microbial Metabolism and Applications
ResumoThe first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1−C25 Diels−Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels−Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.
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