Synthesis of ( - )-sordarin

Abstract

The first total synthesis of ( - )-sordarin 1 has been accomplished by the use of following reactions for key steps: I) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative to construct a bicyclo[5.3.0]decan-3- one skeleton, II) Pd(O)-catalyzed intramolecular allylation reaction to prepare the strained bicyclo[2.2.1]heptan-2-one derivative having the whole framework of sordaricin 2, III) selective dihydroxylation reaction of terminal alkenes by the combined use of OsO4 and PhB(OH)4, and IV) β -(l,2-cis)-selective glycosidation by a 1,3-neighboring participation of a p-methoxybenzoyl group.