title: Total synthesis of the proposed structure of mycosporulone: structural revision and an unexpected retro-aldol/aldol reaction.
abstract: The proposed structure of the fungal metabolite, mycosporulone 1, was prepared starting from the cyclohexenone ester 11 and the D-(R)-glyceraldehyde acetonide 12. The spectroscopic data for both 1 and its C2 epimer 1a did not match those reported for the natural product. A revised structure 29 for mycosporulone is proposed.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Jonah J
authors.initials: JJ
authors.lastname: Chang
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D003510:Cyclohexanes; D013141:Spiro Compounds; C400135:mycosporulone; C116609:3-hydroxybutanal