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  • Title: Total synthesis of (-)-exiguolide.
    Author: Cook C, Guinchard X, Liron F, Roulland E.
    Journal: Org Lett; 2010 Feb 19; 12(4):744-7. PubMed ID: 20078080.
    Abstract:
    The first total synthesis of the naturally occurring enantiomer of exiguolide ((-)-1) has been completed. This very convergent synthesis features the following as main steps: (i) a Trost's ruthenium-catalyzed ene-yne cross-coupling reaction (this complex transformation allows the challenging control of the C5-C28 double bond geometry along with the stereoselective construction of the tetrahydropyran ring A) and (ii) a very efficient one-pot, two-step stereoselective conjugated allylic alcohol substitution that allowed the control of the C15 stereogenic center.
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