2017
DOI: 10.1039/c7ob01732d
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Total syntheses and configuration assignments of JBIR-04 and unantimycin A

Abstract: First total syntheses of JBIR-04 and unantimycin A have been achieved. Comparison of our spectroscopic data with those reported for natural samples verified the structure of the natural products; (2S,4S,6S,7R,9S,28S) configuration was thus assigned via total synthesis.

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Cited by 3 publications
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“…The absolute configuration of the threonine moiety of 1 was elucidated to be L by Marfey’s method; however, the other three stereogenic centers were not determined. During our studies on the total syntheses of antimycin-type antibiotics, we focused on the total synthesis and stereochemical elucidation of 1 . Recently, Awakawa and Abe et al have reported the production of JBIR-06 and related ring-expansion compounds with reprogramming of the antimycin NRPS (nonribosomal peptide synthase)/PKS (polyketide synthase) assembly line .…”
mentioning
confidence: 99%
“…The absolute configuration of the threonine moiety of 1 was elucidated to be L by Marfey’s method; however, the other three stereogenic centers were not determined. During our studies on the total syntheses of antimycin-type antibiotics, we focused on the total synthesis and stereochemical elucidation of 1 . Recently, Awakawa and Abe et al have reported the production of JBIR-06 and related ring-expansion compounds with reprogramming of the antimycin NRPS (nonribosomal peptide synthase)/PKS (polyketide synthase) assembly line .…”
mentioning
confidence: 99%