92979-24-3Relevant academic research and scientific papers
Addition of Crotylchromium(II) and Dilithium Propionate to (R)-2,3-O-isopropylideneglyceraldehyde: Steric Course and Synthetic Application in a Formal Synthesis of (+)- and (-)-δ-Multistriatin
Mulzer, Johann,Lasalle, Peter de,Freissler, Axel
, p. 1152 - 1171 (2007/10/02)
The chromium(II) salt 4a of crotyl bromide adds to (R)-2,3-O-isopropylideneglyceraldehyde (1) with high enantiofacial and low diastereofacial (i.e.Cram) selectivity, whereas dilithium propionate (9) shows the opposite behaviour.The adducts 5, 7, and 10 can be used in a formal synthesis of both enantiomers of the insect pheromone δ-multistriatin (30).
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
Mulzer, Johann,Lasalle, Peter de,Chucholowski, Alexander,Blaschek, Ursula,Bruentrup, Gisela,et al.
, p. 2211 - 2218 (2007/10/02)
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.
