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Title: A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12
Contributor(s): Legendre, Sarah (author); Jevric, Martyn (author); Klepp, Julian (author); Sumby, Christopher J (author); Greatrex, Ben  (author)orcid 
Publication Date: 2018
DOI: 10.1016/j.tet.2017.11.010
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Abstract: A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R∗,3S∗)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (±)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein.
Publication Type: Journal Article
Source of Publication: Tetrahedron, 74(12), p. 1229-1239
Publisher: Pergamon Press
Place of Publication: United Kingdom
ISSN: 1464-5416
Field of Research (FOR): 030401 Biologically Active Molecules
030503 Organic Chemical Synthesis
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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Appears in Collections:Journal Article
School of Rural Medicine

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