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

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
Publication Date
2018
Author(s)
Legendre, Sarah
Jevric, Martyn
Klepp, Julian
Sumby, Christopher J
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Elsevier Ltd
Place of publication
United Kingdom
DOI
10.1016/j.tet.2017.11.010
UNE publication id
une:22969
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.
Link
link
Citation
Tetrahedron, 74(12), p. 1229-1239
ISSN
1464-5416
0040-4020
Start page
1229
End page
1239

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