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Org Lett. 2014 Dec 19;16(24):6488-91. doi: 10.1021/ol503347d. Epub 2014 Dec 9.

Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides.

Author information

1
Department of Chemistry, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.

Abstract

To access the key Ile-Hpa pseudodipeptide motif in hibispeptins, a series of bidentate carboxamide-based auxiliary groups have been explored to facilitate the palladium-catalyzed arylation of unactivated γ-C(sp(3))-H bonds of Ile precursor with aryl iodides. A new pyridylmethylamine-based auxiliary group PR is introduced, which permits the use of more sterically hindered ortho-substituted aryl iodide substrates and can be removed under mild conditions. Pd-catalyzed PR-directed γ-C(sp(3))-H arylation enabled the first total synthesis of hibispeptin A.

PMID:
25487778
DOI:
10.1021/ol503347d
[Indexed for MEDLINE]

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