Total Synthesis of (+/-)-Cylindricine C
A concise synthesis of (+/-)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical alpha-iodoketone carboazidationibis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.
Keywords: Ascidian Clavelina-Cylindrica ; Tricyclic Marine Alkaloids ; Radical Carboazidation ; Cycloaddition Cascade ; (+/-)-Lepadiformine ; (+)-Cylindricine-C ; Cyclization ; (-)-Lepadiformine ; Lepadiformine ; (-)-Cylindricine-C
Record created on 2011-12-16, modified on 2016-08-09