z-logo
Premium
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
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom