The total synthesis of the annonaceous acetogenin, muricatetrocin C.
The total synthesis of the potential antitumour agent muricatetrocin C has provided an ideal stage for the exploitation and development of new chemistry. A convergent synthetic strategy has been realised incorporating three distinct pieces of methodology, these include a highly diastereoselective hetero-Diels-Alder reaction to construct the butenolide terminus, an oxygen to carbon rearrangement to install the trans-2,5-disubstituted tetrahydrofuran ring and a spatial desymmetrisation process to afford the anti-diol unit.
Dixon
Darren J
DJ
Department of Chemistry, University of Cambridge Lensfield Road, Cambridge, CB2 1EW, UK.
Ley
Steven V
SV
Reynolds
Dominic J
DJ
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D005663:Furans; C456579:muricatetrocin C; C004511:butenolide; D015107:4-Butyrolactone