Synthetic studies on the natural products Zoanthamine and Balanol
1997 (English)Doctoral thesis, comprehensive summary (Other academic)
Three main projects are described in this thesis. In the first, a stereocontrolled route tothe marine alkaloid Zoanthamine was studied. A convergent approach based on thechiral starting materials (S)-Perillyl alcohol and (R)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone was developed. Some of the key reactions for control ofstereochemistry were: Sharpless asymmetric epoxidation, [3,3] sigmatropicrearrangement, iodolactonization-elimination, and diastereoselective alkylation.Intermediates corresponding to the C1-C5, C6-C10, and Cll-C24 fragments ofZoanthamine have been synthesized regio- and stereoselectively.
In the second project, the total synthesis of (-) Balanol has been accomplished.Enantioselective synthesis of the hexahydroazepine ring involved introduction of thetwo stereogenic centres via Sharpless asymmetric epoxidation of an acyclic allylicalcohol, followed by acid-catalysed ring-opening of a bicyclic aziridine intermediate.
The third project deals with a further study of the regio- and stereoselective ring-opening reaction discovered in the balanol project. The ring-opening of the three chiralbicyclic systems (one epoxide and two aziridines) was investigated, with a number ofdifferent nucleophiles and counter-ions. In most cases, excellent regio- andstereoselective was observed. The results from DNMR experiments, X-raycrystallography, and molecular mechanics calculations were used to provide anexplanation for the observed selectivity, which is postulated to originate from acombination of steric and electronic factors.
Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 1997. , 48 p.
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 257
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-830ISBN: 91-554-3915-2OAI: oai:DiVA.org:uu-830DiVA: diva2:170961
1997-02-28, the Svedberg Lecture Hall, Institute of Chemistry, Uppsala University, Uppsala, 10:15