[
    {
        "id": "authors:pbh3q-3rv94",
        "collection": "authors",
        "collection_id": "pbh3q-3rv94",
        "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20180601-150432322",
        "type": "article",
        "title": "Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V",
        "author": [
            {
                "family_name": "Myers",
                "given_name": "Andrew G.",
                "clpid": "Myers-A-G"
            },
            {
                "family_name": "Gin",
                "given_name": "David Y.",
                "clpid": "Gin-D-Y"
            },
            {
                "family_name": "Rogers",
                "given_name": "Daniel H.",
                "clpid": "Roegrs-D-H"
            }
        ],
        "abstract": "A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V), Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.",
        "doi": "10.1021/ja00090a018",
        "issn": "0002-7863",
        "publisher": "American Chemical Society",
        "publication": "Journal of the American Chemical Society",
        "publication_date": "1994-06-01",
        "series_number": "11",
        "volume": "116",
        "issue": "11",
        "pages": "4697-4718"
    },
    {
        "id": "authors:687dr-dwx92",
        "collection": "authors",
        "collection_id": "687dr-dwx92",
        "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20180501-151529099",
        "type": "article",
        "title": "A convergent synthetic route to the tunicamycin antibiotics. Synthesis of (+)-tunicamycin V",
        "author": [
            {
                "family_name": "Myers",
                "given_name": "Andrew G.",
                "clpid": "Myers-A-G"
            },
            {
                "family_name": "Gin",
                "given_name": "David Y.",
                "clpid": "Gin-D-Y"
            },
            {
                "family_name": "Rogers",
                "given_name": "Daniel H.",
                "clpid": "Roegrs-D-H"
            }
        ],
        "abstract": "The tunicamycins are a family of natural products represented generally by structure 1, wherein R indicates one of several long-chain branched, linear, saturated or unsaturated acyl substituents. They elicit a considerable range of biological responses including antimicrobial, antifungal, antiviral, and antitumor activities. Their ability to function as potent inhibitors of oligosaccharide synthesis in eukaryotic cells has established them as unique biochemical probes of the role of glycosylation on protein structure and function. In this work, we describe a concise synthetic route to the tunicamycins, illustrated by the preparation of (+)-tunicamycin V (1-V).",
        "doi": "10.1021/ja00058a060",
        "issn": "0002-7863",
        "publisher": "American Chemical Society",
        "publication": "Journal of the American Chemical Society",
        "publication_date": "1993-03-10",
        "series_number": "5",
        "volume": "115",
        "issue": "5",
        "pages": "2036-2038"
    }
]