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  • Title: (-)-Lytophilippine A: synthesis of a C1-C18 building block.
    Author: Gille A, Hiersemann M.
    Journal: Org Lett; 2010 Nov 19; 12(22):5258-61. PubMed ID: 20973508.
    Abstract:
    The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing d-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).
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