xiamycin and indole

xiamycin has been researched along with indole* in 2 studies

Other Studies

2 other study(ies) available for xiamycin and indole

ArticleYear
Toward a Unified Total Synthesis of the Xiamycin and Oridamycin Families of Indolosesquiterpenes.
    The Journal of organic chemistry, 2017, 12-15, Volume: 82, Issue:24

    A unified synthetic strategy toward the oridamycin and xiamycin families of natural products was designed, aiming to access several natural products from a common synthetic intermediate readily prepared from geranyl acetate. Part of this strategy was successfully realized, culminating in the synthesis of oridamycin A and oridamycin B. Key steps include a Mn(III)-mediated oxidative radical cyclization to construct the trans-decalin ring, and a 6π-electrocyclization/aromatization sequence to produce the 2,3-fused carbazole. Oridamycin B was accessed through a late-stage, C-H oxidation that converted the C16 methyl to a hydroxymethyl. A variety of strategies were explored to form a chelated radical intermediate en route to xiamycin A, including enolate SET oxidation, oxo-vanadium oxidation, and atom-transfer cyclization. Unfortunately, none of these strategies provided the desired C16-epimeric trans-decalin. Exploratory studies on photoredox-catalyzed radical cyclizations yielded interesting results, including the formation of a bicyclic lactone arising from oxidative termination of the photoredox-catalyzed radical cyclization, and a double 6-endo cyclization with catalyst loadings as low as 0.01 mol%.

    Topics: Indoles; Molecular Structure; Sesquiterpenes

2017
Elucidating the cyclization cascades in xiamycin biosynthesis by substrate synthesis and enzyme characterizations.
    Organic letters, 2015, Jan-16, Volume: 17, Issue:2

    Indolosesquiterpene xiamycin A features a pentacyclic core structure. The chemical synthesis of two key precursors, 3-farnesylindole and 3-(epoxyfarnesyl)-indole, allowed elucidation of the enzymatic cascades forming the pentacyclic ring system of xiamycin A by XiaO-catalyzed epoxidation and the membrane protein XiaH-catalyzed terpene cyclization. The substrate flexibility of XiaI, an indole oxygenase for assembly of the central ring, was also demonstrated.

    Topics: Biocatalysis; Cyclization; Enzyme Precursors; Epoxy Compounds; Indoles; Membrane Proteins; Molecular Structure; Oxidation-Reduction; Oxidoreductases; Sesquiterpenes; Terpenes

2015