title: Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.
abstract: Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.
authors.affiliation: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.
authors.forename: Sandra F
authors.initials: SF
authors.lastname: Mayer
authors.forename: Andreas
authors.initials: A
authors.lastname: Steinreiber
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
mesh_terms: D000480:Alkynes; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D053280:Diynes; D053281:Enediynes; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D005894:Panax / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000972:Antineoplastic Agents, Phytogenic; D053280:Diynes; D053281:Enediynes; D005233:Fatty Alcohols; C018541:falcarinol; C057682:panaxytriol