Marcel Achtenhagen, Thomas Silldorff, Kit H B Foster, Tayler Barone, Rudrajit Mal, Evon Bolessa, Alexis Ellis, Raman Bahulekar, Nandkumar Deorkar, Erik J Sorensen
A three-step synthesis of squalene (1), the universal precursor of sterols, an adjuvant for vaccines, and a component of cosmetics, has been achieved from plant-derived trans, trans-farnesol (2) and 2-nitrobenzenesulfonamide (3). The successful strategy described herein features an end-to-end pairing of farnesyl radicals formed in one laboratory operation from bis-farnesylamine (6) and Levin's anomeric amide (7). This concise synthesis provides squalene in 99.8% purity after purification of the derived thiourea clathrate, following the procedure of Nicolaides and Laves.