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Studies In The Asymmetric Synthesis Of The C21-C34 Fragment Of The Natural Product, Antascomicin B, Brian Lee Walker
Studies In The Asymmetric Synthesis Of The C21-C34 Fragment Of The Natural Product, Antascomicin B, Brian Lee Walker
Graduate Theses and Dissertations
This dissertation describes studies in the asymmetric synthesis of the C21 – C34 fragment of the natural product, antascomicin B. Antascomicin B is structurally related to FK506, binds strongly to FKBP12, yet does not shown immunosuppressive activity. Small ligand FKBP12 binding complexes were shown to have potent neuroprotective and neuroregenerative properties in mouse models of Parkinson’s disease. The highlighted chemical reactions include an asymmetric transfer hydrogenation (ATH), Ireland-Claisen rearrangement (ICR), directed hydrogenation and allylic diazene rearrangement.
Towards The Total Synthesis Of Antascomicin B. Efforts To Construct The C1-C21 Fragment, Juliette Rivero-Castro
Towards The Total Synthesis Of Antascomicin B. Efforts To Construct The C1-C21 Fragment, Juliette Rivero-Castro
Graduate Theses and Dissertations
Antascomicin B is a macrolide isolated from a strain of Micromonospora. It possesses structural similarities to FK506 and rapamycin and exhibits potent binding ability to FKBP12. Recent reports suggest that small molecule ligands of FKBP12 possess potent neuroprotective and neurodegenerative properties in mouse models of Parkinson's disease. Our approach to the C1-21 fragment of antascomicin B involves an asymmetric amino-Claisen rearrangement originally developed by Tsunoda et al.35 report the scalability of the preparation and rearrangement of an allylic amide possessing a silyloxy group at the terminal position of the alkene. The Tsunoda-Claisen rearrangement uses inexpensive (S)-α-methylbenzylamine as the chiral …