Tetrahydrofuran lignans via tandem oxidative anionic-radical processes or reductive radical cyclizations.
Several tetrahydrofuran lignans have become important due to their diverse biological activities. We present initial studies on short syntheses of some of the simplest members of this natural product class. Galgravin and Veraguensin are obtained in only three or four steps from nitroalkenes and allylic alcohols via a new tandem anionic-radical process, and reductive radical cyclizations of beta-nitro ethers derived from the same precursors are suitable to obtain Galgravin as well as Galbelgin and Ganschisandrin.
Jahn
Ullrich
U
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany. u.jahn@tu-bs.de
Rudakov
Dmytro
D
D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D010084:Oxidation-Reduction
D005663:Furans; D017705:Lignans