78473-72-0Relevant articles and documents
Synthesis of Lignan Lactones by Conjugate Addition of Thioacetal Carbanions to Butenolide
Pelter, Andrew,Ward, Robert S.,Satyanarayana, Panchagnula,Collins, Peter
, p. 643 - 647 (2007/10/02)
The conjugate addition of carbanions derived from arylbis(phenylthio)methanes to butenolide followed by trapping of the enolate anion so generated by a benzyl halide affords adducts (8) containing the basic lignan skeleton.Desulphurisation of these adducts by Raney nickel affords a short efficient synthesis of trans-dibenzylbutyrolactones and this route has been used to prepare enterolactone (9c) and an antitumour lignan (9b), derived from Bursera schlechtendalii.Treatment of the adducts (8) with heavy-metal salts induces cyclisation leading to arylnaphthalene lactones, including retrojusticidin B (13).