The synthesis is reported of 3-s-butyl-4-methyl-3,6,8-trihydroxy-3,4- dihydroisocoumarin (1a) and 3-(1-methyl-prop-1-enyl)-4-methyl-3,6,8-trihydroxy- 3,4-dihydroisocoumarin (1b) using organocopper reagents and anions of 1,3-dithians for compound (1a), and anions of 1,3-dithians and of O-trimethylsilylcyanohydrins for compound (1b). The synthetic methods used represent new means for attaining an extensive range of acetogenins of natural origin and of biogenetic intermediates.
Acetogenin synthesis. Organocopper reagents, anions of 1,3-dithians and of protected cyanohydrins as intermediates in ketide side-chain synthesis / L. Colombo, C.M.A. Gennari, M. Santandrea, E. Narisano, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1980), pp. 136-140. [10.1039/P19800000136]
Acetogenin synthesis. Organocopper reagents, anions of 1,3-dithians and of protected cyanohydrins as intermediates in ketide side-chain synthesis
C.M.A. Gennari;
1980
Abstract
The synthesis is reported of 3-s-butyl-4-methyl-3,6,8-trihydroxy-3,4- dihydroisocoumarin (1a) and 3-(1-methyl-prop-1-enyl)-4-methyl-3,6,8-trihydroxy- 3,4-dihydroisocoumarin (1b) using organocopper reagents and anions of 1,3-dithians for compound (1a), and anions of 1,3-dithians and of O-trimethylsilylcyanohydrins for compound (1b). The synthetic methods used represent new means for attaining an extensive range of acetogenins of natural origin and of biogenetic intermediates.
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