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Total synthesis of (-)-exiguolide.

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Cook, Cyril | Guinchard, Xavier | Liron, Frédéric | Roulland, Emmanuel

Edité par CCSD ; American Chemical Society -

International audience. 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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