Further Syntheses of Optically Active Verrucarinic Acid, 43rd Communication of Verrucarins and Roridins
- 26 September 1984
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 67 (6), 1625-1629
- https://doi.org/10.1002/hlca.19840670631
Abstract
Two new syntheses of verrucarinic acid (2S, 3R‐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 publication has 41 references indexed in Scilit:
- Synthesis of epoxytrichothecenes: verrucarin J and verrucarin J isomersThe Journal of Organic Chemistry, 1984
- A tandem cycloaddition-ene strategy for the synthesis of (.+-.)-verrucarol and (.+-.)-4,11-diepi-12,13-deoxyverrucarolJournal of the American Chemical Society, 1984
- Total synthesis of the trichothecene mycotoxin anguidineJournal of the American Chemical Society, 1983
- Syntheses of Optically Active Verrucarinic Acid. 40th Communication on Verrucarins and RoridinsHelvetica Chimica Acta, 1983
- Synthesis of trichoverrin B and its conversion to verrucarin JThe Journal of Organic Chemistry, 1982
- Stereoselective synthesis of calonectrinJournal of the American Chemical Society, 1982
- High Asymmetric Induction in Conjugate Additions of RCu · BF3 to Chiral Enoates. Preliminary communicationHelvetica Chimica Acta, 1981
- Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communicationHelvetica Chimica Acta, 1981
- A New and Convenient Synthesis of Glyoxals, Glyoxalate Esters, and α-DiketonesJournal of the American Chemical Society, 1966
- Hydrogenolysis of Sulfur Compounds by Raney Nickel CatalystJournal of the American Chemical Society, 1943