Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 52, Pages 17433-17442Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404316
Keywords
aziridinium; diastereoselectivity; reductive amination; substrate and reagent control; total synthesis
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Funding
- National Research Foundation of Korea (NRF) grant - Korean government (MSIP) [2013R1A2A1A01015998]
- National Research Foundation of Korea [2012H1A8002186, 2013R1A2A1A01015998] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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We describe a flexible and divergent route to the pyrrolo-/pyrido[1,2-j] quinoline frameworks of tricyclic marine alkaloids via a common intermediate formed by the ester-enolate Claisen rearrangement of a cyclic amino acid allylic ester. We have synthesized the proposed structure of polycitorols and demonstrated that the structure of these alkaloids requires revision. In addition to asymmetric formal syntheses, stereoselective and concise total syntheses of (-)-lepadi-formine and (-)-fasicularin were also accomplished from simple, commercially available starting materials in a completely substrate-controlled manner. The key step in these total syntheses was the reagent-dependent stereoselective reductive amination of the common intermediate to yield either indolizidines 55a or 55b. Aziridinium-mediated carbon homologation of the hindered C-10 group to the homoallylic group facilitated the synthesis.
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