Studies towards the total synthesis of solanoeclepin A: synthesis and potato cyst nematode hatching activity of analogues containing the tetracyclic left-hand substructureElectronic supplementary information (ESI) available: further experimental details. See http://www.rsc.org/suppdata/p1/b2/b202020n
| Autor: | Floris P. J. T. Rutjes, Jean-François Brière, Richard H. Blaauw, Jorg C. J. Benningshof, Angeline E. van Ginkel, Henk Hiemstra, Sabine R. Wallner, Anne L. Koster, Jan H. van Maarseveen, Maarten IJsselstijn |
|---|---|
| Rok vydání: | 2002 |
| Předmět: | |
| Zdroj: | Journal of the Chemical Society, Perkin Transactions 1. :1701-1713 |
| ISSN: | 1364-5463 1472-7781 |
| DOI: | 10.1039/b202020n |
| Popis: | In our studies towards the total synthesis of solanoeclepin A, a natural hatching agent of potato cyst nematodes, three analogues containing the tetracyclic left-handed substructure have been synthesised. First, the synthesis of the parent tetracycle 2 in enantiopure form is reported. Key steps are (1) chromium-mediated coupling of aldehyde 5 (see preceding paper in this issue) and vinyl triflate 6 to furnish an α,β-unsaturated lactone, which was transformed into triene 4 in six-steps, (2) ring-closing metathesis of 4 to tetracycle 3 and (3) oxidative functionalisation of the least substituted double bond of 3 to provide the fully functionalised tetracyclic left-handed substructure of solanoeclepin A. The methodology developed was successfully applied in the synthesis of two more elaborate solanoeclepin A analogues 9 and 11. Both compounds, prepared as mixtures of diastereomers, showed promising biological activity in hatching activity tests. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|