Straightforward synthesis of sphinganines via a serine-derived Weinreb amide

Regina C So; Rachel Ndonye; Douglas P Izmirian; Stewart K Richardson; Robyn L Guerrera; Amy R Howell

doi:10.1021/jo030355b

Straightforward synthesis of sphinganines via a serine-derived Weinreb amide

J Org Chem. 2004 Apr 30;69(9):3233-5. doi: 10.1021/jo030355b.

Authors

Regina C So¹, Rachel Ndonye, Douglas P Izmirian, Stewart K Richardson, Robyn L Guerrera, Amy R Howell

Affiliation

¹ Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.

PMID: 15104474
DOI: 10.1021/jo030355b

Abstract

Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amides / chemistry*
Ketones / chemistry
Organometallic Compounds / chemistry
Serine / chemistry*
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis*
Stereoisomerism

Substances

Amides
Ketones
Organometallic Compounds
Serine
Sphingosine
safingol