TOTAL SYNTHESIS OF (-)-SLAFRAMINE FROM (2R,3S)-3-HYDROXYPROLINE

Authors
KNIGHT DW SIBLEY AW
Citation
Dw. Knight et Aw. Sibley, TOTAL SYNTHESIS OF (-)-SLAFRAMINE FROM (2R,3S)-3-HYDROXYPROLINE, Journal of the Chemical Society. Perkin transactions. I, (15), 1997, pp. 2179-2187
Citations number
85
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
15
Year of publication
1997
Pages
2179 - 2187
Database
ISI
SICI code
0300-922X(1997):15<2179:TSO(F(>2.0.ZU;2-P
Abstract
The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergo es an efficient Julia olefination with the L-serine-derived amino sulf one 29, Selective reduction of the resulting alkene 31 using diimide a nd cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural(-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.