An enantioselective synthesis and the absolute configuration of natural pumiliotoxin‐C . Preliminary communication | Zendy

Oppolzer Wolfgang | Zendy; Flaskamp Elmar | Zendy

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

Author(s) -

Oppolzer Wolfgang,

Flaskamp Elmar

Publication year - 1977

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19770600123

Subject(s) - enantioselective synthesis , chemistry , enantiomer , norvaline , absolute configuration , stereochemistry , chirality (physics) , total synthesis , cycloaddition , amino acid , organic chemistry , valine , catalysis , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quark , quantum mechanics

(−)‐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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