An enantioselective approach to the Securinega alkaloids: the total synthesis of (+)-norsecurinine and (+)-allonorsecurinine

Abstract

Total syntheses of (+)-norsecurinine and (+)-allonorsecurinine are described that utilize a rhodium carbenoid-initiated O–H insertion/Claisen rearrangement/1,2-allyl migration domino process for the stereoselective introduction of the tertiary alcohol moiety. Overall the employed strategy is flexible and will allow access to other members of the Securinega family of alkaloids.