Total synthesis of (-)-exiguolide.
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.
Cook
Cyril
C
Centre de Recherche CNRS de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Guinchard
Xavier
X
Liron
Frédéric
F
Roulland
Emmanuel
E
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D018942:Macrolides; D009942:Organometallic Compounds; C527475:exiguolide; D012428:Ruthenium