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An enantioselective synthesis and the absolute configuration of natural pumiliotoxin-C. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; Elmar Flaskamp

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
218 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

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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