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

Gang He, Shu Yu Zhang, William A. Nack, Ryan Pearson, Javon Rabb-Lynch, Gong Chen

Research output: Contribution to journalArticle

38 Citations (Scopus)

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(sp3)-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(sp3)-H arylation enabled the first total synthesis of hibispeptin A.

Original languageEnglish (US)
Pages (from-to)6488-6491
Number of pages4
JournalOrganic Letters
Volume16
Issue number24
DOIs
StatePublished - Dec 19 2014

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Iodides
iodides
Palladium
synthesis
palladium
Substrates
hibispeptin A

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

He, G., Zhang, S. Y., Nack, W. A., Pearson, R., Rabb-Lynch, J., & Chen, G. (2014). Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides. Organic Letters, 16(24), 6488-6491. https://doi.org/10.1021/ol503347d
He, Gang ; Zhang, Shu Yu ; Nack, William A. ; Pearson, Ryan ; Rabb-Lynch, Javon ; Chen, Gong. / Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides. In: Organic Letters. 2014 ; Vol. 16, No. 24. pp. 6488-6491.
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He, G, Zhang, SY, Nack, WA, Pearson, R, Rabb-Lynch, J & Chen, G 2014, 'Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides', Organic Letters, vol. 16, no. 24, pp. 6488-6491. https://doi.org/10.1021/ol503347d

Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides. / He, Gang; Zhang, Shu Yu; Nack, William A.; Pearson, Ryan; Rabb-Lynch, Javon; Chen, Gong.

In: Organic Letters, Vol. 16, No. 24, 19.12.2014, p. 6488-6491.

Research output: Contribution to journalArticle

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T1 - Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides

AU - He, Gang

AU - Zhang, Shu Yu

AU - Nack, William A.

AU - Pearson, Ryan

AU - Rabb-Lynch, Javon

AU - Chen, Gong

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Y1 - 2014/12/19

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AB - 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(sp3)-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(sp3)-H arylation enabled the first total synthesis of hibispeptin A.

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