4.8 Article

A Formal Enantioselective Total Synthesis of FR901483

Journal

ORGANIC LETTERS
Volume 14, Issue 18, Pages 4834-4837

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302165d

Keywords

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Funding

  1. NSF of China [20832005, 21072160]
  2. National Basic Research Program (973 Program) of China [2010CB833200]
  3. Fundamental Research Funds for the Central Universities of China [201112G001]

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A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.

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