Journal
ORGANIC LETTERS
Volume 12, Issue 4, Pages 744-747Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902829e
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- Institut de Chimie des Substances Naturelles (ICSN)
- Centre National pour la Recherche Scientifique (CNRS)
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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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