Abstract (−)‐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 (2 S )‐configuration of natural pumiliotoxin‐C.
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Oppolzer et al. (1977) studied this question.
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