Double lawton SN2'addition to epoxyvinyl sulfones: selective construction of the stereotetrads of aplyronine A

[reaction: see text] Enantiopure epoxyvinyl sulfones function as templates for the diastereoselective construction of the three stereotetrads of aplyronine A. Lawton S(N)2' addition of 3,5-dimethylpyrazole followed by its displacement in an alcohol-directed Lawton S(N)2' reaction establish...

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Veröffentlicht in:	Organic letters 2006-07, Vol.8 (14), p.2905-2908
Hauptverfasser:	El-Awa, Ahmad, Fuchs, Philip
Format:	Artikel
Sprache:	eng
Schlagworte:	Epoxy Compounds - chemistry Lactones - chemical synthesis Lactones - chemistry Macrolides Molecular Structure Serine - analogs & derivatives Serine - chemical synthesis Serine - chemistry Stereoisomerism Sulfones - chemistry Vinyl Compounds - chemistry
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Zusammenfassung:	[reaction: see text] Enantiopure epoxyvinyl sulfones function as templates for the diastereoselective construction of the three stereotetrads of aplyronine A. Lawton S(N)2' addition of 3,5-dimethylpyrazole followed by its displacement in an alcohol-directed Lawton S(N)2' reaction establishes the required product stereochemistry with high selectivity.
ISSN:	1523-7060