Total Synthesis of (+)-Neopeltolide by the Macrocyclization/Transannular Pyran Cyclization Strategy
Kazuki Nakazato, Mami Oda, Haruhiko Fuwa
Abstract
An 11-step synthesis of (+)-neopeltolide was developed. The C1–C7 carboxylic acid and the C8–C16 alcohol were prepared, each in six steps, from (R)- and (S)-epichlorohydrin, respectively. After esterification, our tandem macrocyclization/transannular pyran cyclization strategy was applied to a stereocontrolled construction of the neopeltolide macrolactone. The side chain was synthesized in six steps from ethyl 4-oxazolecarboxylate through palladium-catalyzed cross-couplings. A Mitsunobu reaction of the neopeltolide macrolactone and the side chain completed the synthesis.
Topics & Concepts
ChemistryEpichlorohydrinPyranMitsunobu reactionTandemSide chainTotal synthesisAlcoholStereochemistryCombinatorial chemistryOrganic chemistryPolymerComposite materialMaterials scienceSynthetic Organic Chemistry MethodsPlant-derived Lignans Synthesis and BioactivityChemical synthesis and alkaloids