P. Spanu, G. Rassu, L. Pinna
Oct 1, 1997
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0
Influential Citations
24
Citations
Journal
Tetrahedron-asymmetry
Abstract
A twelve-step, diastereoselective synthesis of [(2S,3R,4E)-2-amino-1,3-dihydroxy-4-octadecene, 1] is described (12 steps, 10% overall yield), starting from 3. The first step was the crossed addition of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)pyrrole (TB-SOP, 2) to 3 (a vinylogous variant of the Mukaiyama-aldol reaction) producing a seven-carbon lactam intermediate 4, which was then shortened by three carbon atoms to furnish the aldehydo-erythrose derivative 10. Wittig elongation of 10 with the appropriate C14 ylide, followed by photoinduced Z to E double bond isomerization and removal of the protecting groups, completed the synthesis.