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Further Syntheses of Optically Active Verrucarinic Acid, 43rd Communication of Verrucarins and Roridins
Author(s) -
Grossen Peter,
Herold Peter,
Mohr Peter,
Tamm Christoph
Publication year - 1984
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.19840670631
Subject(s) - chemistry , optically active , regioselectivity , malic acid , glyoxylate cycle , alkylation , stereoselectivity , stereochemistry , organic chemistry , catalysis , enzyme , citric acid
Abstract Two new syntheses of verrucarinic acid (2 S , 3 R ‐dihydroxy‐3‐methylpentanoic acid) and its derivatives, suitably protected for the further conversion to macrocyclic trichothecenes, are described. The first one makes use of a diastereoselective alkylation of a (−)‐( S )‐malic acid ester and the regioselective reductin of one carboxyl function toa methyl group. The second approach involves a stereoselective addition of an allylsilane to a chiral glyoxylate.