The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

Kuniaki Tatsuta, Hiroaki Tanaka, Hitomi Tsukagoshi, Takafumi Kashima, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    20 Citations (Scopus)

    Abstract

    The total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael-Dieckmann type cyclization with the thioester, by which the highly convergent route has been established.

    Original languageEnglish
    Pages (from-to)5546-5549
    Number of pages4
    JournalTetrahedron Letters
    Volume51
    Issue number42
    DOIs
    Publication statusPublished - 2010 Oct 20

    Fingerprint

    Cyclization
    Glycosylation
    Esters
    Alcohols
    Anti-Bacterial Agents
    lactonamycin
    acetylenic alcohol

    Keywords

    • Glycosylation
    • Lactonamycin
    • Michael-Dieckmann type annulation
    • Thioester
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic. / Tatsuta, Kuniaki; Tanaka, Hiroaki; Tsukagoshi, Hitomi; Kashima, Takafumi; Hosokawa, Seijiro.

    In: Tetrahedron Letters, Vol. 51, No. 42, 20.10.2010, p. 5546-5549.

    Research output: Contribution to journalArticle

    Tatsuta, Kuniaki ; Tanaka, Hiroaki ; Tsukagoshi, Hitomi ; Kashima, Takafumi ; Hosokawa, Seijiro. / The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 42. pp. 5546-5549.
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