S-Space College of Pharmacy (약학대학) Dept. of Manufacturing Pharmacy (제약학과) Theses (Ph.D. / Sc.D._제약학과)
Total Synthesis of the Tricyclic Marine Alkaloids Lepadiformine, Fasicularin, and Isomers of Polycitorols by Diastereoselective Reductive Amination.
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- 약학대학 제약학과
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- Ester enolate Clasiene rearrangement ; Reductive amination ; Marine alkaloid ; Azididinium ; Total synthesis
- 학위논문 (박사)-- 서울대학교 대학원 : 약학대학 제약학과, 2016. 2. 김상희.
- Due to their bioactivities and interesting structural features, tricyclic marine alkaloids as (–)-lepadiformine and (–)-fasicularine have been the subject of numerous synthetic studies. In this context, The planning and implementation of flexible, divergent total syntheses of pyrrolo-/pyrido[1,2-j]quinoline tricyclic marine alkaloids is presented. A functionally enriched intermediate was readily assembled by employing an ester-enolate Claisen rearrangement of the cyclic amino acid allylic ester possessing an exocyclic N-carbonyl group. This common intermediate was efficiently converted to (–)-lepadiformine A, (–)-fasicularin, and the proposed structure of recently isolated polycitorols A and B in a substrate-controlled manner. In these studies, we also have shown that the configuration of polycitorols requires revision, proposed possible structure of natural polycitorol A.
A key step in our synthesis was a reagent-dependent stereoselective intramolecular reductive amination of the common intermediate to yield either indolizidines, for syntheis of (–)-lepadiformine and (–)-fasicularin. In addition, less explored aziridinium-mediated carbon homologation of the hindered C-10 group into a homoallylic group greatly facilitated the synthesis.
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