223. “An enantiospecific synthesis of solenopsin A”
     Jefford, C.W.; Wang, J.B.
     Tetrahedron Lett. 1993, 34, 2911-2914.

Enantiomerically pure solenopsin A (1) was prepared in 11 steps from L-aspartic acid (3) in an overall yield of 17%. 6R-(N-tosylamino)heptadecan-2-one (8), prepared from 3, underwent cyclization on acid catalysis to N-tosylamino-2,3-dehydro-2-methyl-6R-undecylpiperidine (9), which on reduction and deprotection gave 1.

L-Aspartic acid (3) was converted to the amino-ketone (8) which on cyclization to (9), reduction and deprotection, gave solenopsin A (1).

DOI : 10.1016/S0040-4039(00)60479-3 

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