Enantioselective preparation of C-ring fragment of cotylenin A via catalytic asymmetric intramolecular cyclopropanation of α-diazo β-keto ester

Kotaro Nagatani, Yunosuke Hoshino, Haruka Tezuka, Masahisa Nakada

    Research output: Contribution to journal › Article

    5 Citations (Scopus)

    Abstract

    A synthetic pathway to the C-ring fragment of cotylenin A which emerged from our retrosynthetic analysis of cotylenin A is described. The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of the α-diazo-β-keto ester bearing 2,4,6-trimethylphenyl group as the ester part has been found to afford the crystalline product with high ee, which allowed to establish the approach to the C-ring fragment which required ten-pot operations. The developed approach would be beneficial to a large scale synthesis of the C-ring fragment for the total synthesis of cotylenin A.

    Original languageEnglish
    Pages (from-to)959-962
    Number of pages4
    JournalTetrahedron Letters
    Volume58
    Issue number10
    DOIs
    Publication statusPublished - 2017 Mar 8

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    Esters
    Bearings (structural)
    Crystalline materials
    cotylenin A

    Keywords

    • Asymmetric catalysis
    • Cotylenin A
    • Cyclopropanation
    • Synthetic studies
    • α-diazo β-keto ester

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Cite this

    Enantioselective preparation of C-ring fragment of cotylenin A via catalytic asymmetric intramolecular cyclopropanation of α-diazo β-keto ester. / Nagatani, Kotaro; Hoshino, Yunosuke; Tezuka, Haruka; Nakada, Masahisa.

    In: Tetrahedron Letters, Vol. 58, No. 10, 08.03.2017, p. 959-962.

    Research output: Contribution to journal › Article

    Nagatani, K, Hoshino, Y, Tezuka, H & Nakada, M 2017, 'Enantioselective preparation of C-ring fragment of cotylenin A via catalytic asymmetric intramolecular cyclopropanation of α-diazo β-keto ester', Tetrahedron Letters, vol. 58, no. 10, pp. 959-962. https://doi.org/10.1016/j.tetlet.2017.01.076
    Nagatani K, Hoshino Y, Tezuka H, Nakada M. Enantioselective preparation of C-ring fragment of cotylenin A via catalytic asymmetric intramolecular cyclopropanation of α-diazo β-keto ester. Tetrahedron Letters. 2017 Mar 8;58(10):959-962. https://doi.org/10.1016/j.tetlet.2017.01.076
    Nagatani, Kotaro ; Hoshino, Yunosuke ; Tezuka, Haruka ; Nakada, Masahisa. / Enantioselective preparation of C-ring fragment of cotylenin A via catalytic asymmetric intramolecular cyclopropanation of α-diazo β-keto ester. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 10. pp. 959-962.
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    AU - Nagatani, Kotaro

    AU - Hoshino, Yunosuke

    AU - Tezuka, Haruka

    AU - Nakada, Masahisa

    PY - 2017/3/8

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    AB - A synthetic pathway to the C-ring fragment of cotylenin A which emerged from our retrosynthetic analysis of cotylenin A is described. The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of the α-diazo-β-keto ester bearing 2,4,6-trimethylphenyl group as the ester part has been found to afford the crystalline product with high ee, which allowed to establish the approach to the C-ring fragment which required ten-pot operations. The developed approach would be beneficial to a large scale synthesis of the C-ring fragment for the total synthesis of cotylenin A.

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