38. An enantioselective synthesis and the absolute configuration of natural pumiliotoxin-C. Preliminary communication
    Oppolzer, W.; Flaskamp, E.
    Helv. Chim. Acta 1977, 60, 204-207

(−)-Pumiliotoxin-C-hydrochloride, as well as its unnatural enantiomer, have been synthesized in an enantioselective manner starting from(S)- or (R)-norvaline, respectively. In the crucial cycloaddition step 11 → 12(cf. scheme 2) the chiral center of 11 controls to a major extent the three developing centers of chirality. This synthesis shows unambigously the (2S)-configuration of natural pumiliotoxin-C.

DOI : 10.1002/hlca.19770600123