Stereocontrolled synthesis of lepadiformine A.
In this paper we present results of a study into whether the tricyclic core of the lepadiformines A-C can be accessed via intramolecular hetero-Diels-Alder cycloaddition. We are able to demonstrate that such a process is possible and that the reaction proceeds in an endo-selective fashion, providing the correct relative stereochemistry for this family of natural products. By employing this approach we have been able to develop a short (7 step) synthesis of (+/-)-lepadiformine A, starting from commercially-available trans-2-nonenal.
Lygo
Barry
B
School of Chemistry, University of Nottingham, Nottingham, UKNG7 2RD.
Kirton
Eirene H M
EH
Lumley
Christopher
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry*
D000470:Alkaloids; D001688:Biological Products; C431548:lepadiformine