Abstract
The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived b-ketophosphonate reagents and their Horner–Wadsworth–Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.
| Original language | English |
|---|---|
| Pages (from-to) | 757-762 |
| Journal | SYNTHESIS: STUTTGART |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2010 |
| MoE publication type | A1 Journal article-refereed |
Keywords
- diastereoselectivity
- enantioselectivity
- sphingosine
- ceramide
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CCDC 255364: Experimental Crystal Structure Determination
Sauerland, S. J. K. (Creator), Castillo-Melendez, J. A. (Creator), Nättinen, K. (Creator), Rissanen, K. (Creator) & Koskinen, A. (Creator), Cambridge Crystallographic Data Centre , 25 Mar 2011
DOI: 10.5517/cc8kqk2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8kqk2&sid=DataCite
Dataset
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CCDC 255365: Experimental Crystal Structure Determination
Karppanen, E. (Creator) & Koskinen, A. (Creator), Cambridge Crystallographic Data Centre , 25 Mar 2011
DOI: 10.5517/cc8kql3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8kql3&sid=DataCite
Dataset