Journal
TETRAHEDRON
Volume 70, Issue 20, Pages 3291-3296Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.10.059
Keywords
Bioprotective agents; L-Leucine; Unsaturated diazoketones; Wolff rearrangement; Diazophosphonates
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Funding
- FAPESP [2012/04685-5, 2012/22274-2]
- CNPq [307905/2009-8]
- IQSC-USP (FAPESP) [2009/54040-8]
- University of Sao Paulo through the NAP-CatSinQ
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [09/54040-8] Funding Source: FAPESP
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An expedited synthesis of the bioprotective agent JP4-039 is described from N-Boc-L-leucinal in 50% overall yield. The synthesis involves the use of an alpha,beta-unsaturated diazoketone as the key intermediate, followed by a photochemical Wolff rearrangement in the presence of 4-amino-TEMPO (4-AT). (C) 2013 Elsevier Ltd. All rights reserved.
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