title: Concise total synthesis of spirocurcasone.
abstract: A concise total synthesis of spirocurcasone was accomplished. Key features of the synthesis involved a vinylogous Mukaiyama aldol reaction, a Carroll rearrangement of β-keto allyl ester derivative, an intramolecular aldol condensation, and a spiro ring formation by ring-closing metathesis of the pentaene compound. This synthetic work was complete in nine steps from (S)- or (R)-perillaldehyde without the use of protecting groups. Interestingly, the optical rotation of the synthetic spirocurcasone was different from the reported value of the natural product.
authors: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors: Hideki
authors: H
authors: Abe
authors: Akimi
authors: A
authors: Sato
authors: Toyoharu
authors: T
authors: Kobayashi
authors: Hisanaka
authors: H
authors: Ito
mesh_terms: D000447:Aldehydes; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D031286:Jatropha / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004224:Diterpenes; D004952:Esters; C556077:spirocurcasone; C116609:3-hydroxybutanal