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  • Title: Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B.
    Author: Shimizu T, Satoh T, Murakoshi K, Sodeoka M.
    Journal: Org Lett; 2005 Dec 08; 7(25):5573-6. PubMed ID: 16320994.
    Abstract:
    [chemical reaction: see text]. The stereocontrolled total synthesis of (-)-spirofungin A (1) and (+)-spirofungin B (2a), polyketide-type antibiotics having various antifungal activities, has been achieved employing the Weinreb amide 8, the alkyne 9, and the vinyl boronate 5 readily available from the common intermediate 10. The first synthesis proceeded with a longest linear sequence of 31 steps, affording (-)-1 and (+)-2a in 7.9% and 5.2% overall yields, respectively.
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