Synthesis of (±)-Secosyrin 1 and a Formal Synthesis of (−)-Secosyrin 1

Abstract

[reaction: see text] A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.