Stereoselective additions to carboxylic acid dianions and β-lactone substituted ester enolatesApplication to the synthesis of racemic epi-blastmycinone, δ-multistriatine,paraconic esters and lignantype dilactones |
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| Authors: | Johann Mulzer Peter De Lasalle Alexander Chucholowski Ursula Blaschek Gisela Brüntrup Ibrahim Jibril Gottfried Huttner |
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| Affiliation: | Institut für Organische Chemie der Universität Düsseldorf Universitätsstrasse 1, D-4000 Düsseldorf 1, Federal Republic of Germany;Lehrstuhl für Synthetische Anorganische Chemie, Fakultät für Chemie der Universität Konstanz, Postfach 5560, D-7750 Konstanz Federal Republic of Germany |
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| Abstract: | New stereoselective syntheses are reported for racemic 4-epi-blastmycinone (6) and δ-multistriatine (13) utilizing the anti-configurated γ, β-unsaturated β-hydroxy-carboxylic acids 2a/b. A diastereo- and enantioselective aldoltype addition of phenylacetic acid dianion to benzaldehyde has been achieved by employing optically active alkoxide amide bases. Finally, highly stereocontrolled additions to the novel β-lactone substituted ester enolates 22 are described. |
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