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Total Synthesis of (−)‐Decarbamoyloxysaxitoxin
Author(s) -
Iwamoto Osamu,
Koshino Hiroyuki,
Hashizume Daisuke,
Nagasawa Kazuo
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703326
Subject(s) - natural product , yield (engineering) , cycloaddition , enantiomer , combinatorial chemistry , total synthesis , chemistry , organic chemistry , stereochemistry , materials science , catalysis , metallurgy
A facile and general synthetic strategy for saxitoxin derivatives has been developed, as exemplified by the efficient synthesis of (−)‐decarbamoyloxysaxitoxin ((−)‐doSTX), the putative enantiomer of the natural product, in 17 steps and in 10 % overall yield. The synthesis features a diastereoselective 1,3‐dipolar cycloaddition and a direct oxidation with o ‐iodoxybenzoic acid (IBX; see scheme, Cbz=benzyloxycarbonyl).