STEREOSELECTIVE ADDITIONS TO CARBOXYLIC ACID DIANIONS AND β-LACTONE SUBSTITUTED ESTER ENOLATES. APPLICATION TO THE SYNTHESIS OF RACEMIC EPI-BLASTMYCINONE, δ-MULTISTRIATINE, PARACONIC ESTERS AND LIGNANTYPE DILACTONES

DOI: 10.1016/0040-4020(84)80003-4

Source and publish data:

Tetrahedron p. 2211 - 2218 (1984)

Update date:2022-08-05

Topics:

Authors:

Mulzer, Johann

Lasalle, Peter de

Chucholowski, Alexander

Blaschek, Ursula

Bruentrup, Gisela

et al. et al.

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Article abstract of DOI:10.1016/0040-4020(84)80003-4

New stereoselective syntheses are reported for racemic 4-epi-blastmycinone (6) and δ-multistriatine (13) utilizing the anti-configurated γ,δ-unsaturated β-hydroxy-carboxylic acids 2a/b.A diastereo- and enantioselective aldoltype addition of phenylacetic acid dianion to benzaldehyde has been achaived by employing optically active alkoxide amide bases.Finally, highly stereocontrolled additions to the novel β-lactone substituted ester enolates 22 are described.

Full text of DOI:10.1016/0040-4020(84)80003-4

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