jorunnamycin-a and jorumycin

jorunnamycin-a has been researched along with jorumycin* in 2 studies

Other Studies

2 other study(ies) available for jorunnamycin-a and jorumycin

ArticleYear
Concise total syntheses of (-)-jorunnamycin A and (-)-jorumycin enabled by asymmetric catalysis.
    Science (New York, N.Y.), 2019, 01-18, Volume: 363, Issue:6424

    The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.

    Topics: Antineoplastic Agents; Catalysis; Cell Line, Tumor; Drug Discovery; Humans; Hydrogenation; Isoquinolines; Molecular Structure; Quinolones; Tetrahydroisoquinolines

2019
Asymmetric total synthesis of (-)-jorunnamycins A and C and (-)-jorumycin from L-tyrosine.
    Journal of natural products, 2013, Sep-27, Volume: 76, Issue:9

    Three renieramycin-type antitumor alkaloids, (-)-jorunnamycins A (1) and C (2) and (-)-jorumycin (3), have been synthesized by a new convergent approach, which features a highly regio- and stereoselective Pictet-Spengler cyclization to couple the isoquinoline and the trisubstituted phenylalaninol partners. This synthetic strategy opens an economical access to these important antitumor alkaloids with high yields: (-)-jorunnamycin A, as a common precursor to other renieramycin-type alkaloids and their analogues, is obtained with 18.1% overall yield from l-tyrosine.

    Topics: Alkaloids; Cyclization; Isoquinolines; Molecular Structure; Quinolones; Quinones; Stereoisomerism; Tetrahydroisoquinolines; Tyrosine

2013