Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7'-hydroxylignano-9,9'-lactones.
The asymmetric synthesis of a series of (7'S,8R,8'R)-7'-hydroxylignano-9,9'-lactones is presented, among them the mammalian lignan (7'S)-hydroxyenterolactone and (7'S)-parabenzlactone, allowing the stereochemistry of natural occurring (-)-parabenzlactone to be re-assigned. A hydroxylactone rearrangement and its possible mechanisms are discussed. Finally a brief survey of the current naming and numbering variants of 7'-hydroxylignano-9,9'-lactones is presented, along with a suggestion for harmonization of the nomenclature.
Raffaelli
Barbara
B
Department of Chemistry, Laboratory of Organic Chemistry, University of Helsinki, P.O. Box 55, FIN-00014, Finland.
Wähälä
Kristiina
K
Hase
Tapio
T
D000818:Animals; D001688:Biological Products / Q000737:chemistry; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis*; D017705:Lignans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D009626:Terminology as Topic
D001688:Biological Products; D007783:Lactones; D017705:Lignans