Toward the Total Synthesis of Klaivanolide: Complete Reinterpretation of Its Originally Assigned Structure

• Published in: European journal of organic chemistry Vol. 2014; no. 28; pp. 6183 - 6189
• Main Authors: Ferrié, Laurent, Ferhi, Sabrina, Bernadat, Guillaume, Figadère, Bruno
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Organic; Density functional calculations; Lactones; Physical Sciences; Science & Technology; Structure elucidation; Total synthesis; Vibrational spectroscopy; RING-CLOSING METATHESIS; BIOACTIVE HEPTENES; THERMOCHEMISTRY; CHEMISTRY; Density functional calculations; HYDROXYMETHYLATION; Structure elucidation; Total synthesis; Lactones; Vibrational spectroscopy
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201402741

Klaivanolide is an antiparasitic natural product isolated from Uvaria klaineana, whose structure was originally assigned as a seven‐membered lactone ring. Attempts towards the total synthesis of klaivanolide led us to revise its original structural assignment based on both experimental evidence and spectroscopic data. The isolated compound was revealed to be a known molecule, acetylmelodorinol, originally isolated from Melodorum fruticosum. Vibrational circular dichroism simulation of the reassigned structure was also performed to reinvestigate our previous studies on the determination of the absolute configuration of klaivanolide. Attempts towards the total synthesis of uncommon seven‐membered ring lactone klaivanolide led us to revise its original structural assignment. The isolated compound was revealed to be a known molecule, the five‐membered ring acetylmelodorinol.