4.8 Article

Synthesis of Fully Substituted Polyhydroxylated Pyrrolizidines via Cope-House Cyclization

Journal

ORGANIC LETTERS
Volume 13, Issue 16, Pages 4414-4417

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201749c

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Funding

  1. Summit PLC (UK)
  2. National Basic Research Program of China [2009CB526511, 2011CB808603]
  3. Ministry of Science and Technology
  4. Ministry of Health of the P.R. China [2009ZX09501-006]

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Total synthesis of the proposed structure of (-)-hyacinthacine C-5 and its epimers at C6 and C7 is described. A key step of the synthesis was the construction of the bicyclic pyrrolizidine system by means of a nucleophilic addition of a dithiane to a cyclic nitrone followed by a Cope House cyclization.

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