Literature DB >> 15104474

Straightforward synthesis of sphinganines via a serine-derived Weinreb amide.

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

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.

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Year:  2004        PMID： 15104474     DOI： 10.1021/jo030355b

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

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Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

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Authors:  Carter G Eiden; Courtney C Aldrich
Journal:  J Org Chem       Date:  2017-07-26       Impact factor: 4.354

5.  Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.

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Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

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Journal:  Chem Biol       Date:  2008-07-21

7.  Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-sphinganine, (+)-spisulosine, and D-ribo-phytosphingosine.

Authors:  Ewen D D Calder; Ahmed M Zaed; Andrew Sutherland
Journal:  J Org Chem       Date:  2013-07-03       Impact factor: 4.354

8.  Identification of a Dual Inhibitor of Secreted Phospholipase A2 (GIIA sPLA2) and SARS-CoV-2 Main Protease.

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  8 in total

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